OBT / Orange County Bancorp, Inc. - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

Orange County Bancorp, Inc.
US ˙ NasdaqCM ˙ US68417L1070

Mga Batayang Estadistika
CIK 1754226
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Orange County Bancorp, Inc.
SEC Filings (Chronological Order)
Halaman ini menyediakan daftar lengkap dan kronologis dari Pengajuan SEC, tidak termasuk pengajuan kepemilikan yang kami sediakan di tempat lain.
September 5, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 2, 2025 Orange County B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 2, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorporation) (Commissi

August 27, 2025 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY., August 27, 2025 – Orange County Bancorp, Inc. (Nasdaq: OBT), parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc. today announced a declaration of a $0.13 cash dividend per share of its common stock. The dividend will be paid on September 16, 2025 to sharehold

August 27, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 27, 2025 Orange County Ban

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 27, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S

August 11, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 00

July 30, 2025 EX-99.1

ORANGE COUNTY BANCORP, INC.

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Record Second Quarter 2025 earnings: • Net Income increased $2.3 million, or 27.4%, to $10.5 million for the quarter ended June 30, 2025 from $8.2 million for the quarter ended June 30, 2024 • Net Interest Income grew $1.0 million, or 4.2%, to $25.1 million for the quarter ended June 30, 2025, as compared to $24.1 million for

July 30, 2025 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): July 30, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S.

June 30, 2025 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 11-K FOR ANNUAL REPORTS OF EMPLOYEE STOCK PURCHASE, SAVINGS AND SIMILAR PLANS PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 11-K FOR ANNUAL REPORTS OF EMPLOYEE STOCK PURCHASE, SAVINGS AND SIMILAR PLANS PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ☒ ANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 15(d) OF TH

June 9, 2025 EX-99.1

Orange County Bancorp, Inc. Announces Closing of Overallotment Option and Issuance of 258,064 Shares of Common Stock

EXHIBIT 99.1 Orange County Bancorp, Inc. Announces Closing of Overallotment Option and Issuance of 258,064 Shares of Common Stock MIDDLETOWN, NEW YORK – June 9, 2025 –– Orange County Bancorp, Inc. (the “Company” - Nasdaq: OBT), parent company of Orange Bank & Trust Company, (the “Bank”) and Hudson Valley Investment Advisors, Inc. (“HVIA”), today announced that the underwriters for its recently com

June 9, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 9, 2025 Orange County Bancor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 9, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

June 4, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 3, 2025 Orange County Bancor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 3, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

June 4, 2025 424B5

1,720,430 Shares Common Stock

TABLE OF CONTENTS  Filed pursuant to Rule 424(b)(5)  Registration Statement No. 333-280793 PROSPECTUS SUPPLEMENT To Prospectus dated July 19, 2024 1,720,430 Shares Common Stock Orange County Bancorp, Inc. is offering 1,720,430 shares of our common stock, $0.25 par value per share. Our common stock is listed for trading on the Nasdaq Capital Market, under the symbol “OBT.” On June 2, 2025, the last

June 4, 2025 EX-99.2

Orange County Bancorp, Inc. Announces Pricing of Public Offering of Common Stock

Exhibit 99.2 Orange County Bancorp, Inc. Announces Pricing of Public Offering of Common Stock MIDDLETOWN, NEW YORK – June 3, 2025 –– Orange County Bancorp, Inc. (the “Company” - Nasdaq: OBT), parent company of Orange Bank & Trust Company, (the “Bank”) and Hudson Valley Investment Advisors, Inc. (“HVIA”), today announced the pricing of an underwritten public offering of 1,720,430 shares of its comm

June 4, 2025 EX-1.1

Underwriting Agreement, dated as of June 3, 2025, by and among Orange County Bancorp, Inc., Orange Bank & Trust Company and Piper Sandler & Co., as representative of the underwriters named therein.

Exhibit 1.1 Execution Version ORANGE COUNTY Bancorp, Inc. 1,720,430 Shares of Common Stock $0.25 Par Value Per Share Underwriting Agreement June 3, 2025 PIPER SANDLER & CO. 1251 Avenue of the Americas, 6th Floor New York, New York 10022 as representative of the Underwriters names in Schedule I hereto. Ladies and Gentlemen: Orange County Bancorp, Inc., a Delaware corporation (the “Company”), the ho

June 4, 2025 EX-99.1

Orange County Bancorp, Inc. Launches Public Offering of Common Stock

Exhibit 99.1 Orange County Bancorp, Inc. Launches Public Offering of Common Stock MIDDLETOWN, NEW YORK – June 3, 2025 –– Orange County Bancorp, Inc. (the “Company” - Nasdaq: OBT), parent company of Orange Bank & Trust Company, (the “Bank”) and Hudson Valley Investment Advisors, Inc. (“HVIA”), today announced it launched an underwritten public offering of shares of its common stock. The Company als

June 3, 2025 FWP

INVESTOR Presentation June 2025 Follow - On Offering of Common Stock Safe Harbor Statement and Disclaimer Notice to and Undertaking by Recipients This presentation has been prepared by Orange County Bancorp, Inc. (the “Company” or “Orange”) solely fo

Filed Pursuant to Rule 433 Issuer Free Writing Prospectus dated June 3, 2025 Relating to Preliminary Prospectus Supplement dated June 3, 2025 and Prospectus dated July 19, 2024 Registration No.

June 3, 2025 424B5

SUBJECT TO COMPLETION, DATED JUNE 3, 2025

TABLE OF CONTENTS The information in this preliminary prospectus supplement is not complete and may be changed.

May 20, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 20, 2025 Orange County Bancor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 20, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

May 16, 2025 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY., May 16, 2025 – Orange County Bancorp, Inc. (Nasdaq: OBT), parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc. today announced a declaration of a $0.13 cash dividend per share of its common stock. The dividend will be paid on June 16, 2025 to shareholders of r

May 16, 2025 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 16, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

May 12, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 0

April 30, 2025 8-K

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): April 30, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorporation) (Commission

April 30, 2025 EX-99.1

ORANGE COUNTY BANCORP, INC.

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces First Quarter 2025 Earnings: Highlights include - • Net interest margin of 3.95% for the quarter ended March 31, 2025 increased 31 basis points, or 8.5%, versus 3.64% for the quarter ended March 31, 2024 • Total Deposits grew $128.3 million, or 6.0%, reaching $2.3 billion at March 31, 2025 as compared to $2.2 billion at Decem

April 23, 2025 EX-10.1

SALE AND PURCHASE AGREEMENT

Exhibit 10.1 SALE AND PURCHASE AGREEMENT AGREEMENT made this 17th day of April, 2025, by and between ORANGE BANK & TRUST COMPANY, a New York banking corporation having an address at 212 Dolson Avenue, Middletown, New York 10940 (hereinafter referred to as “Seller”), and JRTN PROPERTIES LLC having an address at 8 Parsons Way, Slate Hill, New York 10973, (hereinafter referred to as “Purchaser”). 1.

April 23, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): April 17, 2025 Orange County Banc

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): April 17, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorporation) (Commission

April 11, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

March 17, 2025 EX-19

Insider Trading

Exhibit 19 ORANGE COUNTY BANCORP, INC. POLICY REGARDING INSIDER TRADING Orange County Bancorp, Inc. (the “Company”) is a public company, the common stock of which is listed on the Nasdaq Capital Market and registered under the Securities Exchange Act of 1934, as amended. As a public company, the Company files periodic reports and proxy statements with the Securities and Exchange Commission (the “S

March 17, 2025 EX-21

Subsidiaries of Registrant

Exhibit 21 Subsidiaries of the Registrant The following is a list of the subsidiaries of Orange County Bancorp, Inc.: NameState of Incorporation Orange Bank & Trust CompanyNew York Hudson Valley Investment Advisors, Inc.New York

March 17, 2025 10-K

e UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

Table of Contents e UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

February 26, 2025 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 20, 2025 ORANGE COUNTY BANCORP, INC. (Exact Name of Registrant as Specified in Its Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) of Incorporation) (Commission File N

February 26, 2025 EX-10.2

Amendment dated February 20, 2025, to the Amended and Restated Participation Agreement for Michael J. Gilfeather under the Orange Bank & Trust Company Performance-Based Supplemental Executive Retirement Plan

EXHIBIT 10.2 Amendment #1 to the Participation Agreement by and Between Michael Gilfeather and Orange Bank & Trust Company for Participation in the Orange Bank & Trust Company Performance-based Supplemental Executive Retirement Plan WHEREAS, Orange Bank & Trust Company (the “Bank”) maintains Orange Bank & Trust Company Performance-Based Supplemental Executive Retirement Plan (the “Plan”) for the b

February 26, 2025 EX-10.1

Amendment dated February 20, 2025, to the Amended and Restated Employment Agreement, dated effective as of January 1, 2024, by and among Orange County Bancorp, Inc., Orange Bank & Trust Company and Michael J. Gilfeather

EXHIBIT 10.1 Amendment to the Amended and Restated Employment Agreement by and between Orange County Bancorp, Inc., Orange Bank & Trust Company and Michael J. Gilfeather WHEREAS, Orange County Bancorp, Inc. (“Company”), Orange Bank & Trust Company ("Bank") and Michael J. Gilfeather ("Executive") entered into an employment agreement originally effective as of December 31, 2018, amended and restated

February 21, 2025 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY., February 21, 2025 – Orange County Bancorp, Inc. (Nasdaq: OBT), parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc. today announced a declaration of a $0.13 cash dividend per share of its common stock. The dividend will be paid on March 17, 2025 to shareholder

February 21, 2025 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 21, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

February 5, 2025 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 5, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.

February 5, 2025 EX-99.1

ORANGE COUNTY BANCORP, INC.

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Fourth Quarter and Full-Year Earnings for Fiscal 2024: • Net Interest Income increased $3.4 million, or 3.8%, to $91.8 million for the year ended December 31, 2024, from $88.4 million for the year ended December 31, 2023 • Net Interest Margin grew 5 basis points to 3.83% for the year ended December 31, 2024, from 3.78% for th

January 10, 2025 EX-3.1

Amendment to the Certificate of Incorporation of Orange County Bancorp, Inc. (incorporated by reference to Exhibit 3.1 to the Current Report on Form 8-K of Orange County Bancorp, Inc. (File No. 001-40711), filed with the Securities and Exchange Commission on January 10, 2025)

Exhibit 3.1 CERTIFICATE OF AMENDMENT OF CERTIFICATE OF INCORPORATION OF ORANGE COUNTY BANCORP, INC. (a Delaware corporation) Orange County Bancorp, Inc., a Delaware corporation (the “Corporation”), does hereby certify: First: The name of the Corporation is Orange County Bancorp, Inc. Second: The Board of Directors of the Corporation, acting in accordance with Sections 141(f) and 242 of the General

January 10, 2025 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): January 10, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorporation) (Commissio

January 2, 2025 8-K

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): January 2, 2025 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorporation) (Commission

January 2, 2025 EX-99.1

Orange County Bancorp, Inc. Adjusts Stock Split Record Date as US Markets Close on January 9 in Honor of National Day of Mourning for Former President Jimmy Carter

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Adjusts Stock Split Record Date as US Markets Close on January 9 in Honor of National Day of Mourning for Former President Jimmy Carter MIDDLETOWN, N.Y., January 2, 2025 – Orange County Bancorp, Inc. (the “Company” - Nasdaq: OBT), parent company of Orange Bank & Trust Co. and Hudson Valley Investment Advisors, Inc., today announced tha

December 26, 2024 EX-99.1

1

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Two-for-One Stock Split MIDDLETOWN, N.Y., December 26, 2024 – Orange County Bancorp, Inc. (the “Company” - Nasdaq: OBT), parent company of Orange Bank & Trust Co. and Hudson Valley Investment Advisors, Inc., today announced that its Board of Directors declared a two-for-one forward stock split (the “Stock Split”) of the Compan

December 26, 2024 8-K

Financial Statements and Exhibits

8-K 1 form8k.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 26, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorpo

November 22, 2024 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): November 21, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorporation) (Commissi

November 22, 2024 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY., November 22, 2024 – Orange County Bancorp, Inc. (Nasdaq: OBT), parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc. today announced a $0.02 increase and a declaration of a $0.25 cash dividend per share of its common stock. The dividend will be paid on December

November 13, 2024 EX-99.1

INVESTOR Presentation November 2024

Exhibit 99.1 INVESTOR Presentation November 2024 Safe Harbor Statement and Disclaimer Forward - Looking Statements This presentation contains, and future oral and written statements by us and our management may contain, forward - looking stateme nts within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. These forward - looking statem

November 13, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): November 13, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

November 13, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numbe

October 30, 2024 EX-99.1

ORANGE COUNTY BANCORP, INC. SUMMARY OF AUM/AUA (Dollar Amounts in thousands)

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Third Quarter 2024 results: • Net Interest Income increased $467 thousand, or 2.1%, to $23.0 million for the quarter ended September 30, 2024, from $22.5 million for the quarter ended September 30, 2023 • Net Interest Margin grew 3 basis points to 3.81% for the quarter ended September 30, 2024, as compared to 3.78% for the qu

October 30, 2024 8-K

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): October 30, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorporation) (Commissio

September 25, 2024 EX-99.1

Orange County Bancorp, Inc. Announces the Appointment of Jon Schiller to the Board of Directors

EXHIBIT 99.1 Orange County Bancorp, Inc. Announces the Appointment of Jon Schiller to the Board of Directors MIDDLETOWN, N.Y. – September 25, 2024 — Orange County Bancorp, Inc. (the "Company") (NASDAQ:OBT), parent company of Orange Bank & Trust Co. (the "Bank") announced today the appointment of Jonathan Schiller, RPh, MBA, to the Company’s and the Bank’s Boards of Directors effective October 1, 2

September 25, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 19, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.

August 16, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 15, 2024 Orange County Ban

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 15, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S

August 16, 2024 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY – On August 15, 2024, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.23 cash dividend per share of its common stock. The dividend will be paid on September 16, 2024 to shareholders o

August 12, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 00

July 31, 2024 8-K

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): July 31, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S.

July 31, 2024 EX-99.1

ORANGE COUNTY BANCORP, INC.

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Second Quarter 2024 results: • Net Interest Income increased $1.5 million, or 6.7%, to $24.1 million for the quarter ended June 30, 2024 from $22.6 million for the quarter ended June 30, 2023 • Net Interest Margin grew 29 basis points, or 7.6%, to 4.10% for the quarter ended June 30, 2024, as compared to 3.81% for the quarter

July 17, 2024 CORRESP

Orange County Bancorp, Inc. 212 Dolson Avenue Middletown, New York 10940

Orange County Bancorp, Inc. 212 Dolson Avenue Middletown, New York 10940 July 17, 2024 Via Edgar Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Orange County Bancorp, Inc. Registration Statement on Form S-3 (Registration No. 333-280793) Request for Acceleration of Effectiveness Ladies and Gentlemen: Orange County Bancorp, Inc., a Delaware corporation (the “Company

July 12, 2024 S-3

As filed with the Securities and Exchange Commission on July 12, 2024

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on July 12, 2024 Registration No.

July 12, 2024 POS AM

As filed with the Securities and Exchange Commission on July 12, 2024

As filed with the Securities and Exchange Commission on July 12, 2024 Registration No.

July 12, 2024 EX-4.4

Form of Indenture for Senior Debt Securities

Exhibit 4.4 ORANGE COUNTY BANCORP, INC., AS ISSUER AND [    ], AS TRUSTEE SENIOR INDENTURE DATED AS OF [ ], 20[ ] SENIOR DEBT SECURITIES CROSS-REFERENCE TABLE Reconciliation and tie between the Trust Indenture Act of 1939, as amended (the “Trust Indenture Act”), and the Indenture dated as of [ ], 20[ ]. SECTION OF TRUST INDENTURE ACT SECTION OF INDENTURE 310(a)(1) and (2) 7.09 310(a)(3) and (4) No

July 12, 2024 EX-4.6

Form of Indenture for Subordinated Debt Securities

Exhibit 4.6 ORANGE COUNTY BANCORP, INC., AS ISSUER AND [   ], AS TRUSTEE SUBORDINATED INDENTURE DATED AS OF [   ], 20[   ] SUBORDINATED DEBT SECURITIES CROSS-REFERENCE TABLE Reconciliation and tie between the Trust Indenture Act of 1939, as amended (the “Trust Indenture Act”), and the Indenture dated as of [   ], 20[   ]. SECTION OF TRUST INDENTURE ACT SECTION OF INDENTURE 310(a)(1) and (2) 7.09 3

July 12, 2024 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) Orange County Bancorp, Inc.

June 28, 2024 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 11-K FOR ANNUAL REPORTS OF EMPLOYEE STOCK PURCHASE, SAVINGS AND SIMILAR PLANS PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 11-K FOR ANNUAL REPORTS OF EMPLOYEE STOCK PURCHASE, SAVINGS AND SIMILAR PLANS PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ☒ ANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 15(d) OF TH

June 21, 2024 EX-3.3

Text of 2023 Amendment to the Bylaws of Orange County Bancorp, Inc.

EXHIBIT 3.3 June 15, 2023 Bylaw Amendment Article IV, Section 2 of the Bylaws, is amended to read as follows: ARTICLE IV BOARD OF DIRECTORS Section 2. Qualifications. Each director shall be at least eighteen (18) years of age. Subject to availability, each director shall at all times own shares of common stock of the Corporation in accordance with the Non-Executive Director and Executive Officer S

June 21, 2024 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 17, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S.

June 21, 2024 EX-3.1

Amended and Restated Bylaws of Orange County Bancorp, Inc.

EXHIBIT 3.1 AMENDED AND RESTATED BYLAWS OF ORANGE COUNTY BANCORP, INC. ARTICLE I OFFICES Section 1. Registered Office. The registered office of Orange County Bancorp, Inc. (the "Corporation") in the State of Delaware shall be in the City of Wilmington, County of New Castle. Section 2. Other Offices. The Corporation may also have offices at such other places both within and without the State of Del

June 21, 2024 EX-3.2

Text of 2022 Amendment to the Bylaws of Orange County Bancorp, Inc.

EXHIBIT 3.2 June 17, 2022 Bylaw Amendment Article IV, Section 2 of the Bylaws, is amended to read as follows: ARTICLE IV BOARD OF DIRECTORS Section 2. Qualifications. Each director shall be at least eighteen (18) years of age. Subject to availability, each director shall at all times own shares of common stock of the Corporation having a value equal to at least $125,000. Each director of the Corpo

June 20, 2024 EX-99.1

INVESTOR Presentation June 2024

Exhibit 99.1 INVESTOR Presentation June 2024 Safe Harbor Statement and Disclaimer . Forward - Looking Statements This presentation contains, and future oral and written statements by us and our management may contain, forward - looking stateme nts within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. These forward - looking statemen

June 20, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 20, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S.

May 23, 2024 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 21, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

May 17, 2024 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY – On May 16, 2024, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.23 cash dividend per share of its common stock. The dividend will be paid on June 14, 2024 to shareholders of record

May 17, 2024 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 16, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

May 15, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 0

May 1, 2024 EX-99.1

ORANGE COUNTY BANCORP, INC.

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Record First Quarter Earnings: Highlights include - • Net Income of $9.3 million for the three months ended March 31, 2024 increased $6.1 million, or 187.6%, as compared to $3.2 million for the three months ended March 31, 2023 • Total Deposits grew $110.7 million, or 5.4%, reaching $2.2 billion at March 31, 2024 as compared

May 1, 2024 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 1, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. Em

April 12, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

March 29, 2024 EX-10.15

Orange Bank & Trust Company Change in Control Severance Plan for Senior Executives+

Exhibit 10.15 ORANGE BANK & TRUST BANK CHANGE IN CONTROL SEVERANCE PLAN FOR SENIOR EXECUTIVES 1.Name, Purpose, Eligibility and Effective Date 1.1Name and Purpose of Plan. The purpose of this Orange Bank & Trust Bank Change in Control Severance Plan for Senior Executives (this “Plan”) is to secure the continued services of certain full-time senior executives and key employees of the Bank and its pa

March 29, 2024 10-K

e UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

Table of Contents e UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

March 29, 2024 EX-97

Policy Relating to Recovery of Erroneously Awarded Compensation

Exhibit 97 ORANGE COUNTY BANCORP, INC. RECOUPMENT POLICY EFFECTIVE November 16, 2023 1.Policy Purpose; Effective Date and Retroactive Application. The purpose of this Orange County Bancorp, Inc. (the “Company”) Recoupment Policy (this “Policy”) is to enable the Company to recoup Erroneously Awarded Compensation in the event that the Company is required to prepare an Accounting Restatement. This Po

March 29, 2024 EX-21

Subsidiaries of Registrant

Exhibit 21 Subsidiaries of the Registrant The following is a list of the subsidiaries of Orange County Bancorp, Inc.: NameState of Incorporation Orange Bank & Trust CompanyNew York Hudson Valley Investment Advisors, Inc.New York

February 27, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 21, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorporation) (Commissi

February 21, 2024 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY – On February 15, 2024, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.23 cash dividend per share of its common stock. The dividend will be paid on March 15, 2024 to shareholders of

February 21, 2024 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 15, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

February 13, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 8, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorporation) (Commissio

February 9, 2024 SC 13G/A

OBT / Orange County Bancorp, Inc. / BANC FUNDS CO LLC - NONE Passive Investment

SC 13G/A 1 doc1.htm NONE UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Orange County Bancorp (Name of Issuer) COMMON STOCK (Title of Class of Securities) 68417L107 (CUSIP Number) December 31, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule

February 8, 2024 SC 13G/A

OBT / Orange County Bancorp, Inc. / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

SC 13G/A 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2 )* Orange County Bancorp, Inc (Name of Issuer) Common Stock (Title of Class of Securities) 68417L107 (CUSIP Number) December 29, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate

February 1, 2024 8-K

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): January 31, 2024 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.

February 1, 2024 EX-99.1

ORANGE COUNTY BANCORP, INC.

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Fourth Quarter and Record Full-Year Earnings for Fiscal 2023: Select Highlights include - • Net Income of $29.5 million for the year ended December 31, 2023 represents an increase of $5.1 million, or 21.0%, as compared to $24.4 million for the year ended December 31, 2022 • Net interest margin of 3.78% for the year ended Dece

December 29, 2023 EX-10.2

Amended and Restated Employment Agreement by and between Orange Bank & Trust Company and Joseph A. Ruhl, dated as of December 22, 2023 (incorporated by reference to Exhibit 10.2 to the Current Report on Form 8-K of Orange County Bancorp, Inc. (File No. 001-40711), filed with the Securities and Exchange Commission on December 29, 2023)+

EXHIBIT 10.2 AMENDED AND RESTATED EMPLOYMENT AGREEMENT This Employment Agreement by and between Orange Bank & Trust Company (the “Bank”) and Joseph Ruhl (“Executive”) originally entered into effective January 1, 2018 and amended on December 31, 2020 is hereby amended and restated effective December 22, 2023 (the “Agreement”). Any reference to the “Company” shall mean Orange County Bancorp, Inc. or

December 29, 2023 EX-10.3

Amended and Restated Participation Agreement under the Orange Bank & Trust Company Performance-Based Supplemental Executive Retirement Plan for Michael J. Gilfeather (incorporated by reference to Exhibit 10.3 to the Current Report on Form 8-K of Orange County Bancorp, Inc. (File No. 001-40711), filed with the Securities and Exchange Commission on December 29, 2023)+

EXHIBIT 10.3 AMENDED AND RESTATED PARTICIPATION AGREEMENT UNDER THE ORANGE BANK & TRUST COMPANY PERFORMANCE-BASED SUPPLEMENTAL EXECUTIVE RETIREMENT PLAN THIS PARTICIPATION AGREEMENT by and between ORANGE BANK & TRUST COMPANY (the “Bank”), and MICHAEL GILFEATHER, an executive of Orange County Bancorp, Inc. (the “Company”) and the Bank (referred to herein as the “Participant” and the “Executive”) wa

December 29, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 22, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

December 29, 2023 EX-10.1

Amended and Restated Employment Agreement by and between Orange County Bancorp, Inc., Orange Bank & Trust Company and Michael J. Gilfeather, dated as of December 22, 2023 (incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K of Orange County Bancorp, Inc. (File No. 001-40711) filed with the Securities and Exchange Commission on December 29, 2023)+

EXHIBIT 10.1 AMENDED AND RESTATED EMPLOYMENT AGREEMENT This Employment Agreement by and between Orange County Bancorp, Inc., a Delaware corporation (the “Company”), Orange Bank & Trust Company, a wholly-owned subsidiary of the Company (the “Bank”) and Michael J. Gilfeather (“Executive”) was originally effective as of December 31, 2018, amended and restated effective December 31, 2021 and is hereby

December 28, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 21, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

December 19, 2023 8-K

Temporary Suspension of Trading Under Registrant's Employee Benefit Plans, Financial Statements and Exhibits

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 19, 2023 ORANGE COUNTY BANCORP, INC. (Exact Name of Registrant as Specified in Its Charter) Delaware 001-40711 33-1145559 (State or other jurisdiction of (Commission File Number) (I.R.S. E

December 19, 2023 EX-99.1

IMPORTANT NOTICE CONCERNING THE ORANGE COUNTY BANCORP, INC. 401(K) PLAN AND YOUR ABILITY TO TRADE SHARES OF ORANGE COUNTY BANCORP, INC. SECURITIES

Exhibit 99.1 IMPORTANT NOTICE CONCERNING THE ORANGE COUNTY BANCORP, INC. 401(K) PLAN AND YOUR ABILITY TO TRADE SHARES OF ORANGE COUNTY BANCORP, INC. SECURITIES December 19, 2023 This notice is being sent to all executive officers and directors of Orange County Bancorp, Inc. in accordance with Section 306(a) of the Sarbanes-Oxley Act of 2002 and Rule 104 of Securities and Exchange Regulation BTR. I

November 16, 2023 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY – On November 16, 2023, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.23 cash dividend per share of its common stock. The dividend will be paid on December 15, 2023 to shareholders

November 16, 2023 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): November 16, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

November 16, 2023 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): November 16, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

November 16, 2023 EX-99.1

INVESTOR Presentation November 2023

Exhibit 99.1 INVESTOR Presentation November 2023 Forward Looking Statements 2 Forward - Looking Statements This presentation contains, and future oral and written statements by us and our management may contain, forward - looking stateme nts within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. These forward - looking statemen ts re

November 14, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numbe

October 25, 2023 EX-99.1

September 30, 2023

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Results for Q3, 2023: • Net Income increased $1.2 million, or 15.1%, to $9.0 million for the quarter ended September 30, 2023 from $7.9 million for the quarter ended September 30, 2022 • Net interest margin increased 8 basis points, or 2.2%, reaching 3.78% for the quarter ended September 30, 2023 from 3.70% for the quarter en

October 25, 2023 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): October 25, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.

September 27, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 21, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.

September 27, 2023 EX-99.1

ORANGE COUNTY BANCORP, INC. APPOINTS OLGA LUZ TIRADO TO BOARD OF DIRECTORS Appointment Reflects Bank’s Continuous Bronx-Based Growth

EXHIBIT 99.1 NEWS Contact: Michael Johnston Co-Communications (617) 549-0639 [email protected] ORANGE COUNTY BANCORP, INC. APPOINTS OLGA LUZ TIRADO TO BOARD OF DIRECTORS Appointment Reflects Bank’s Continuous Bronx-Based Growth MIDDLETOWN, N.Y. – September 27, 2023 – Orange County Bancorp, Inc. (the "Company") (NASDAQ:OBT), parent company of Orange Bank & Trust Co. (the "Bank") announ

August 18, 2023 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY – On August 17, 2023, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.23 cash dividend per share of its common stock. The dividend will be paid on September 15, 2023 to shareholders o

August 18, 2023 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 17, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S

August 11, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 00

August 4, 2023 EX-10.2

Form of Restricted Stock Unit Agreement (Non-Employee Directors)

EXHIBIT 10.2 FORM OF ORANGE COUNTY BANCORP, INC. 2023 EQUITY INCENTIVE PLAN RESTRICTED STOCK UNIT AGREEMENT (NON-EMPLOYEE DIRECTORS) Orange County Bancorp, Inc. (“Company”) has awarded you the number of Restricted Stock Units specified, and on the terms noted below, in consideration for your services (“RSU Award”). Your RSU Award is subject to all of the terms and conditions as set forth herein an

August 4, 2023 EX-10.3

Form of Restricted Stock Unit Agreement (Employee/Consultants)

EXHIBIT 10.3 FORM OF ORANGE COUNTY BANCORP, INC. 2023 EQUITY INCENTIVE PLAN RESTRICTED STOCK UNIT AGREEMENT (EMPLOYEE/CONSULTANTS) Orange County Bancorp, Inc. (“Company”) has awarded you the number of Restricted Stock Units specified, and on the terms noted below, in consideration for your services (“RSU Award”). Your RSU Award is subject to all of the terms and conditions as set forth herein and

August 4, 2023 EX-10.4

Form of Performance Restricted Stock Unit Agreement (Employee)

EXHIBIT 10.4 FORM OF ORANGE COUNTY BANCORP, INC. 2023 EQUITY INCENTIVE PLAN PERFORMANCE AWARD AGREEMENT (EMPLOYEE) Orange County Bancorp, Inc. (“Company”) has awarded you Performance Shares (“Performance Award”), subject to all of the terms and conditions as set forth herein and in the Orange County Bancorp, Inc. 2023 Equity Incentive Plan (“Plan”). A copy of the Plan and related prospectus will b

August 4, 2023 EX-FILING FEES

Filing Fee Table

EXHIBIT 107 Calculation of Filing Fee Tables Form S-8 (Form Type) Orange County Bancorp, Inc.

August 4, 2023 S-8

As filed with the Securities and Exchange Commission on August 4, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT THE SECURITIES ACT OF 1933 Orange County Bancorp, Inc. (Exact Name of Regis

Registration No. 333- As filed with the Securities and Exchange Commission on August 4, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in its Charter) Delaware 26-1135778 (State or Other Jurisdiction of (I.R.S. Employer Identification No.

July 26, 2023 EX-99.1

June 30, 2023

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Record Results for Q2, 2023: • Net Income increased $7.0 million, or 330.6%, to $9.1 million for the quarter ended June 30, 2023 from $2.1 million for the quarter ended June 30, 2022 • Total Assets grew $206.6 million, or 9.0%, to $2.5 billion at June 30, 2023 from $2.3 billion at year-end 2022 • Total Loans grew $143.7 milli

July 26, 2023 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): July 26, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 01-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

June 29, 2023 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 11-K FOR ANNUAL REPORTS OF EMPLOYEE STOCK PURCHASE, SAVINGS AND SIMILAR PLANS PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 11-K FOR ANNUAL REPORTS OF EMPLOYEE STOCK PURCHASE, SAVINGS AND SIMILAR PLANS PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ☒ ANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the fiscal year ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 15(d) OF TH

June 26, 2023 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 26, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S.

June 26, 2023 EX-99.1

ORANGE COUNTY BANCORP, INC. ANNOUNCES INCLUSION IN RUSSELL 2000 INDEX Significant Milestone Reflects Bank’s Continued Growth

EXHIBIT 99.1 ORANGE COUNTY BANCORP, INC. ANNOUNCES INCLUSION IN RUSSELL 2000 INDEX Significant Milestone Reflects Bank’s Continued Growth MIDDLETOWN, N.Y. – June 26, 2023 – Orange County Bancorp, Inc. (the "Company") (NASDAQ:OBT), parent company of Orange Bank & Trust Co. (the "Bank") and Hudson Valley Investment Advisors, Inc. ("HVIA") announced today it has been added to the Russell 2000® Index,

June 21, 2023 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 21, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S.

June 21, 2023 EX-99.1

INVESTOR Presentation June 2023

Exhibit 99.1 INVESTOR Presentation June 2023 Forward Looking Statements 2 Forward - Looking Statements This presentation contains, and future oral and written statements by us and our management may contain, forward - looking stateme nts within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. These forward - looking statemen ts repres

May 24, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 23, 2023 Orange County Bancor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 23, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

May 19, 2023 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY – On May 18, 2023, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.23 cash dividend per share of its common stock. The dividend will be paid on June 14, 2023 to shareholders of record

May 19, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 18, 2023 Orange County Bancor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 18, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

May 15, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 0

May 1, 2023 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 1, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. Em

May 1, 2023 EX-99.1

March 31, 2023

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces First Quarter 2023 Results: • Net Interest Income increased $4.8 million, or 29.4%, to $21.1 million for the quarter ended March 31, 2023 from $16.3 million for the quarter ended March 31, 2022 • Total Assets grew $167.0 million, or 7.3%, to $2.5 billion at March 31, 2023 as compared to $2.3 billion at year-end 2022. • Loans

April 14, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

DEF 14A 1 tm232120-1def14a.htm DEF 14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as

March 24, 2023 EX-21

Subsidiaries of Registrant

Exhibit 21 Subsidiaries of the Registrant The following is a list of the subsidiaries of Orange County Bancorp, Inc.: NameState of Incorporation Orange Bank & Trust CompanyNew York Hudson Valley Investment Advisors, Inc.New York

March 24, 2023 10-K

e UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

Table of Contents e UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

February 17, 2023 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 16, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

February 17, 2023 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

EX-99.1 2 tm237288d1ex99-1.htm EXHIBIT 99.1 Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY – On February 16, 2023, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.23 cash dividend per share of its common stock. The dividend will b

February 7, 2023 SC 13G/A

OBT / Orange County Bancorp, Inc. / BANC FUNDS CO LLC - NONE Passive Investment

SC 13G/A 1 doc1.htm NONE UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 01)* Orange County Bancorp (Name of Issuer) COMMON STOCK (Title of Class of Securities) 68417L107 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rul

February 6, 2023 SC 13G/A

OBT / Orange County Bancorp, Inc. / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* Orange County Bancorp, Inc (Name of Issuer) Common Stock (Title of Class of Securities) 68417L107 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which

January 25, 2023 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): January 25, 2023 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.

January 25, 2023 EX-99.1

December 31, 2022

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Record Quarterly and Annual Earnings : • Net income for Q4 2022 reached a quarterly record $9.1 million, a $3.6 million, or 65.0% increase, over net income of $5.5 million in Q4 2021, due primarily to increased interest income • Net income for fiscal year 2022 reached a record $24.4 million, a $3.1 million, or 14.4% increase,

December 29, 2022 EX-10.1

Orange Bank & Trust Company Non-Qualified Deferred Compensation Plan (incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K of Orange County Bancorp, Inc. (File No. 001-40711) filed with the Securities and Exchange Commission on December 29, 2022)+

EX-10.1 2 ex10-18k122322.htm ORANGE BANK & TRUST COMPANY NON-QUALIFIED DEFERRED COMPENSATION PLAN EXHIBIT 10.1 ORANGE BANK & TRUST COMPANY NON-QUALIFIED DEFERRED COMPENSATION PLAN Article I Purpose The Board of Directors of Orange Bank & Trust Company (the “Bank”) has adopted the Orange Bank & Trust Company Non-qualified Deferred Compensation Plan (“Plan”) to permit eligible executives to defer re

December 29, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 23, 2022 ORANGE COUNTY BANCORP, INC.

December 21, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 15, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

December 21, 2022 EX-99.1

Orange County Bancorp, Inc. Announces Retirement of CFO Robert Peacock in 2023 SVP Chief Accounting Officer and Controller, Michael Lesler to assume CFO role

EXHIBIT 99.1 Orange County Bancorp, Inc. Announces Retirement of CFO Robert Peacock in 2023 SVP Chief Accounting Officer and Controller, Michael Lesler to assume CFO role MIDDLETOWN, N.Y. ? December 21, 2022 ? Orange County Bancorp, Inc. (the "Company") (NASDAQ:OBT), parent company of Orange Bank & Trust Co. (the "Bank") announced today the retirement of Robert Peacock, Senior Executive Vice Presi

December 13, 2022 CORRESP

Orange County Bancorp, Inc. 212 Dolson Avenue Middletown, New York 10940

Orange County Bancorp, Inc. 212 Dolson Avenue Middletown, New York 10940 December 13, 2022 Via Edgar Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Orange County Bancorp, Inc. Registration Statement on Form S-3 (Registration No. 333-268635) Request for Acceleration of Effectiveness Ladies and Gentlemen: Orange County Bancorp, Inc., a Delaware corporation (the “Com

December 13, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 12, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

December 1, 2022 S-3

As filed with the Securities and Exchange Commission on December 1, 2022

S-3 1 tm2231534-1s3.htm S-3 TABLE OF CONTENTS As filed with the Securities and Exchange Commission on December 1, 2022 Registration No. 333-          UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-3 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Orange County Bancorp, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdi

December 1, 2022 EX-4.4

Form of Indenture for Senior Debt Securities

Exhibit 4.4 ORANGE COUNTY BANCORP, INC., AS ISSUER AND [??? ], AS TRUSTEE SENIOR INDENTURE DATED AS OF [ ], 20[ ] SENIOR DEBT SECURITIES CROSS-REFERENCE TABLE Reconciliation and tie between the Trust Indenture Act of 1939, as amended (the ?Trust Indenture Act?), and the Indenture dated as of [ ], 20[ ]. SECTION OF TRUST INDENTURE ACT SECTION OF INDENTURE 310(a)(1) and (2) 7.09 310(a)(3) and (4) No

December 1, 2022 EX-4.6

Form of Indenture for Subordinated Debt Securities

EX-4.6 3 tm2231534d2ex4-6.htm EXHIBIT 4.6 Exhibit 4.6 ORANGE COUNTY BANCORP, INC., AS ISSUER AND [   ], AS TRUSTEE SUBORDINATED INDENTURE DATED AS OF [   ], 20[   ] SUBORDINATED DEBT SECURITIES CROSS-REFERENCE TABLE Reconciliation and tie between the Trust Indenture Act of 1939, as amended (the “Trust Indenture Act”), and the Indenture dated as of [   ], 20[   ]. SECTION OF TRUST INDENTURE ACT SEC

December 1, 2022 EX-FILING FEES

Filing Fee Table

EX-FILING FEES 6 tm2231534d2exfilingfees.htm EX-FILING FEES Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered (1)(2) Proposed Maximum Aggregate Offering Price Per Share (1)(2) Maximum Aggreg

November 18, 2022 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): November 17, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

November 18, 2022 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY ? On November 17, 2022, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.23 cash dividend per share of its common stock. The dividend will be paid on December 15, 2022 to shareholders

November 10, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

November 8, 2022 EX-99.1

November 2022

Exhibit 99.1 November 2022 Forward Looking Statements Forward - Looking Statements This presentation contains, and future oral and written statements by us and our management may contain, forward - looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. These forward - looking statements represent plans, estimates,

November 8, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): November 8, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.

October 25, 2022 EX-99.1

September 30, 2022

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Record Third Quarter Results: ? Net income for Q3 2022 reached a quarterly record $7.9 million, an increase of $2.3 million, or 40.8%, from net income of $5.6 million for Q3 2021, driven primarily by increased net interest income during the quarter ? Total assets increased $225.8 million, or 10.5%, to $2.4 billion at Septembe

October 25, 2022 8-K

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): October 25, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.

September 20, 2022 EX-99.1

Orange County Bancorp, Inc. Announces the Appointment of Marianna R. Kennedy to the Board of Directors

Exhibit 99.1 Orange County Bancorp, Inc. Announces the Appointment of Marianna R. Kennedy to the Board of Directors MIDDLETOWN, N.Y. ? September 20, 2022 ? The Board of Directors and President and CEO Michael Gilfeather of Orange County Bancorp, Inc. (the ?Company? - Nasdaq: OBT), parent company of Orange Bank & Trust Company (the ?Bank?) are pleased to announce the appointment of Marianna R. Kenn

September 20, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 20, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.

September 20, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 15, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.

September 20, 2022 EX-99.1

Stephens Inc. Bank Forum September 2022

Exhibit 99.1 Stephens Inc. Bank Forum September 2022 Forward Looking Statements Forward - Looking Statements This presentation contains, and future oral and written statements by us and our management may contain, forward - looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. These forward - looking statements re

August 26, 2022 EX-FILING FEES

Fee Filings Table

EX-FILING FEES 3 ex107-s8082622.htm FILING FEES TABLE Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount to be Registered(1) Proposed Maximum Aggregate Offering Price Per Share(2) Maximum Aggregate Offe

August 26, 2022 S-8

As filed with the Securities and Exchange Commission on August 26, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT THE SECURITIES ACT OF 1933 Orange County Bancorp, Inc. (Exact Name of Regi

Registration No. 333- As filed with the Securities and Exchange Commission on August 26, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in its Charter) Delaware 26-1135778 (State or Other Jurisdiction of Incorporation or Organization) (I.

August 19, 2022 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 18, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S

August 19, 2022 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY ? On August 18, 2022, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.20 cash dividend per share of its common stock. The dividend will be paid on September 15, 2022 to shareholders o

August 11, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

August 1, 2022 EX-99.1

June 30, 2022

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Second Quarter Results: ? Total Assets increased $250 million, or 11.7%, to $2.4 billion at June 30, 2022 from $2.1 billion at December 31, 2021 ? Total Loans grew $180 million, or 13.9%, to $1.5 billion at June 30, 2022 from $1.3 billion at December 31, 2021 ? Total Deposits reached $2.2 billion at June 30, 2022, as compared

August 1, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 1, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S.

June 30, 2022 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 30, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S.

June 30, 2022 EX-99.1

Orange County Bancorp, Inc. Announces New Board Chair Appointments

EXHIBIT 99.1 Orange County Bancorp, Inc. Announces New Board Chair Appointments MIDDLETOWN, N.Y. ? June 30, 2022 ? Orange County Bancorp, Inc. (the "Company") (NASDAQ:OBT), parent company of Orange Bank & Trust Co. (the "Bank") and Hudson Valley Investment Advisors, Inc. ("HVIA"), is pleased to announce the appointment of Jonathan Rouis as new board chair of both the Company?s and Bank?s board of

June 29, 2022 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 11-K FOR ANNUAL REPORTS OF EMPLOYEE STOCK PURCHASE, SAVINGS AND SIMILAR PLANS PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 11-K FOR ANNUAL REPORTS OF EMPLOYEE STOCK PURCHASE, SAVINGS AND SIMILAR PLANS PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ?? ANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the fiscal year ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 15(d) OF T

May 25, 2022 8-K

Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 24, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

May 20, 2022 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 20, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. E

May 20, 2022 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

Exhibit 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY ? May 20, 2022 ? On May 19, 2022, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.20 cash dividend per share of its common stock. The dividend will be paid on June 15, 2022 to shareho

May 11, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

May 5, 2022 8-K/A

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A Amendment No.1 CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 4, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission Fil

May 5, 2022 EX-99.1

May 2022

Exhibit 99.1 May 2022 Forward Looking Statements Forward - Looking Statements This presentation contains, and future oral and written statements by us and our management may contain, forward - looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. These forward - looking statements represent plans, estimates, objec

May 4, 2022 EX-99.1

May 2022

Exhibit 99.1 May 2022 Forward Looking Statements Forward - Looking Statements This presentation contains, and future oral and written statements by us and our management may contain, forward - looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. These forward - looking statements represent plans, estimates, objec

May 4, 2022 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 4, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S. Em

April 27, 2022 EX-99.1

March 31, 2022

EX-99.1 2 ex99-18k042722.htm PRESS RELEASE DATED APRIL 27, 2022 EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces First Quarter Results: • Net Income for Q1 2022 increased $305 thousand, or 6.1%, over Q1 2021 to $5.3 million • Annualized return on average assets for Q1 2022 declined 18 basis points to 0.95% as compared to 1.13% for the same quarter in 2021 as a result of the

April 27, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): April 27, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S.

April 19, 2022 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) ? Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

March 30, 2022 EX-21

Subsidiaries of Registrant

Exhibit 21 Subsidiaries of the Registrant ? The following is a list of the subsidiaries of Orange County Bancorp, Inc.: ? NameState of Incorporation Orange Bank & Trust CompanyNew York Hudson Valley Investment Advisors, Inc.New York ?

March 30, 2022 EX-10.3

Change in Control Agreement by and between Orange Bank & Trust Company and Robert Peacock, effective as of February 18, 2022 (incorporated by reference to Exhibit 10.3 to the Annual Report on Form 10-K of Orange County Bancorp, Inc. (File No. 001-40711) filed with the Securities and Exchange Commission on March 30, 2022)+

Exhibit 10.3 CHANGE IN CONTROL AGREEMENT This CHANGE IN CONTROL AGREEMENT (the ?Agreement?) made as of this 18th, day of February, 2022 (the ?Effective Date?), by and among ORANGE BANK & TRUST COMPANY, a wholly owned subsidiary of the Company (the ?Bank?) and Robert Peacock (the ?Executive?). For purposes of this Agreement, references to the Company shall mean ORANGE COUNTY BANCORP, INC. WITNESSET

March 30, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

Table of Contents ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

March 30, 2022 EX-10.7

Employment Agreement by and between Hudson Valley Investment Advisors, Inc. and Gustave J. Scacco, effective as of January 30, 2015(incorporated by reference to Exhibit 10.7 to the Annual Report on Form 10-K of Orange County Bancorp, Inc. (File No. 001-40711) filed with the Securities and Exchange Commission on March 30, 2022)+

Exhibit 10.7 EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (the "Agreement") is executed as of this 30th day of January 2015 by and between Hudson Valley Investment Advisors, Inc., a New York corporation, with its principal office at 117 Grand Street, Goshen, NY 10924 ("HVIA" or the "Company"), and Gustave J. Scacco (the "Executive"). ? WHEREAS, the Board of Directors of HVIA desires to employ th

March 30, 2022 EX-4.6

Description of Registrant’s Securities (incorporated by reference to Exhibit 4.6 to the Annual Report on Form 10-K of Orange County Bancorp, Inc. (File No. 001-40711) filed with the Securities and Exchange Commission on March 30, 2022)

Exhibit 4.6 DESCRIPTION OF CAPITAL STOCK ? The following is a summary of the material terms of our capital stock and related provisions of our Certificate of Incorporation and Bylaws. This discussion may not contain all of the information regarding our capital stock that is important to you. Reference is made to the more detailed provisions of our Certificate of Incorporation and Bylaws, copies of

February 25, 2022 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 24, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction of Incorporation) (Commissi

February 25, 2022 EX-99.1

Orange Bank & Trust Promotes Elizabeth Jones to Senior Vice President and Chief Operating Officer

Exhibit 99.1 Orange Bank & Trust Promotes Elizabeth Jones to Senior Vice President and Chief Operating Officer MIDDLETOWN, N.Y. ? February 24, 2022 ? Orange Bank & Trust Company (the ?Bank?), the banking subsidiary of Orange County Bancorp, Inc. (the ?Company? - Nasdaq: OBT), is pleased to announce the promotion of Elizabeth Jones to the role of Senior Vice President and Chief Operating Officer of

February 18, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 18, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

February 18, 2022 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY ? On February 18, 2022, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a $0.20 cash dividend per share of its common stock. The dividend will be paid on March 15, 2022 to shareholders of

February 14, 2022 SC 13G

OBT / Orange County Bancorp, Inc. / Morrison Robert W - SCHEDULE 13G DECEMBER 31, 2021 Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Orange County Bancorp, Inc. (Name of Issuer) Common Stock, par value $0.50 per share (Title of Class of Securities) 68417L107 (CUSIP Number) August 4, 2021 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the

February 11, 2022 SC 13G

OBT / Orange County Bancorp, Inc. / BANC FUNDS CO LLC - NONE Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. n/a )* Orange County Bancorp (Name of Issuer) COMMON STOCK (Title of Class of Securities) 68417L107 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which thi

February 4, 2022 SC 13G

OBT / Orange County Bancorp, Inc. / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Orange County Bancorp, Inc (Name of Issuer) Common Stock (Title of Class of Securities) 68417L107 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which th

January 27, 2022 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): January 26, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.

January 27, 2022 EX-99.1

December 31, 2021

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Record Earnings for 2021: ? Net Income for full year 2021 increased $9.6 million, or 82.1%, to a record $21.3 million ? Return on average assets for Q4 2021 rose 21 basis points, or 25.9%, year-over-year to 1.02% ? Return on average equity for Q4 2021 rose 185 basis points, or 18.1%, year-over-year to 12.08% ? Average Loans (

January 24, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): January 21, 2022 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.

January 24, 2022 EX-99.1

Orange County Bancorp, Inc. Announces the Appointment of Kevin J. Keane to the Board of Directors

EXHIBIT 99.1 Orange County Bancorp, Inc. Announces the Appointment of Kevin J. Keane to the Board of Directors MIDDLETOWN, N.Y. ? January 21, 2022 ? The Board of Directors and CEO Michael Gilfeather of Orange County Bancorp, Inc. (the ?Company? - Nasdaq: OBT), parent company of Orange Bank & Trust Company (the ?Bank?) are pleased to announce the appointment of Kevin J. Keane to the Company?s Board

January 6, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 30, 2021 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

January 6, 2022 EX-10

Employment Agreement by and between Orange County Bancorp, Inc., Orange Bank & Trust Company and Michael J. Gilfeather, dated December 31, 2021

EX-10 2 ex10-8k123021.htm EMPLOYMENT AGREEMENT BY AND BETWEEN ORANGE COUNTY BANCORP, INC., ORANGE BANK & TRUST COMPANY AND MICHAEL J. GILFEATHER, DATED DECEMBER 31, 2021 EXHIBIT 10 EMPLOYMENT AGREEMENT This Employment Agreement originally effective as of December 31, 2018 is hereby amended and restated in its entirety effective December 31, 2021 (the “Agreement”), by and between Orange County Banc

December 29, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 23, 2021 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

December 29, 2021 EX-99.1

Orange Bank & Trust Hires Michael Lesler as SVP, Controller & Chief Accounting Officer

EXHIBIT 99.1 Orange Bank & Trust Hires Michael Lesler as SVP, Controller & Chief Accounting Officer MIDDLETOWN, N.Y. ? December 29, 2021 ? Orange County Bancorp, Inc. (the ?Company? - Nasdaq: OBT), parent company of Orange Bank & Trust Co. (the ?Bank?) announces that Michael Lesler has joined the Company and the Bank as SVP, Controller and Chief Accounting Officer. Michael will report to Robert Pe

November 22, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): November 19, 2021 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R

November 22, 2021 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY ? On November 19, 2021, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a 20? cash dividend per share of its common stock. The dividend will be paid on December 15, 2021 to shareholders of

November 9, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

October 25, 2021 8-K

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): October 25, 2021 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.

October 25, 2021 EX-99.1

ORANGE COUNTY BANCORP, INC. SUMMARY OF LOAN PORTFOLIO SEGMENTS AND DEFERMENTS (UNAUDITED) (Dollar Amounts in thousands) Total Deferments as of September 30, 2021 Industry Classification September 30, 2021 Balance Loan Count % of Total Loans Outstandi

EXHIBIT 99.1 FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Record Third Quarter 2021 Results ? Net Income for Q3 2021 increased $2.6 million, or 91.4%, to a record $5.6 million versus Q3 2020 ? Return on average assets for Q3 2021 rose 35 basis points year-over-year to 1.07% ? Return on common equity for Q3 2021 rose 6.8%, or 126%, year-over-year to 12.2% ? Average Loans (net of PPP)

September 22, 2021 EX-99.1

Stephens Inc. Bank Forum September 2021

Exhibit 99.1 Stephens Inc. Bank Forum September 2021 Forward Looking Statements Forward - Looking Statements This presentation contains, and future oral and written statements by us and our management may contain, forward - looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. These forward - looking statements re

September 22, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 22, 2021 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.

September 22, 2021 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 22, 2021 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.

September 15, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

August 23, 2021 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 20, 2021 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S

August 23, 2021 EX-99.1

Orange County Bancorp, Inc. Declares Cash Dividend

FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Declares Cash Dividend Middletown, NY ? On August 20, 2021, the Board of Directors of Orange County Bancorp, Inc., the parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., declared a 20? cash dividend per share of its common stock. The dividend will be paid on September 15, 2021 to shareholders of record on Sep

August 16, 2021 EX-99.1

ORANGE COUNTY BANCORP, INC.

FOR IMMEDIATE RELEASE Orange County Bancorp, Inc. Announces Record Second Quarter 2021 Results ? Net Income for Q2 2021 increased $2.3 million, or 80.4%, to a record $5.2 million versus Q2 2020 ? Return on average assets for Q2 2021 rose 28 basis points year-over-year to 1.05% ? Return on common equity for Q2 2021 rose 603 basis points year-over-year to 15.0% ? Provision for loan losses of $809 th

August 16, 2021 8-K

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2021 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S

August 10, 2021 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 4, 2021 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Charter) Delaware 001-40711 26-1135778 (State or Other Jurisdiction) (Commission File No.) (I.R.S.

August 10, 2021 EX-99.2

Orange County

Orange County Bancorp, Inc. Orange County Bancorp, Inc. Announces Closing of Initial Public Offering of Common Stock and Full Exercise of Underwriters? Overallotment Option Middletown, N.Y. ? August 9, 2021 ? Orange County Bancorp, Inc. (Nasdaq: OBT) (the ?Company?), parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., today announced the closing of its initia

August 10, 2021 EX-99.1

Orange County

Orange County Bancorp, Inc. Orange County Bancorp, Inc. Announces Pricing of Upsized Initial Public Offering of Common Stock Middletown, N.Y. ? August 4, 2021 ? Orange County Bancorp, Inc. (the ?Company?), parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc., today announced the pricing of its initial public offering of 1,000,000 shares of its common stock at a

August 10, 2021 S-8

As filed with the Securities and Exchange Commission on August 10, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDERTHE SECURITIES ACT OF 1933 Orange County Bancorp, Inc. (Exact Name of

Registration No. 333- As filed with the Securities and Exchange Commission on August 10, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDERTHE SECURITIES ACT OF 1933 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in its Charter) Delaware 26-1135778 (State or Other Jurisdiction of Incorporation or Organization) (I.R

August 5, 2021 424B4

1,000,000 Shares COMMON STOCK

TABLE OF CONTENTS ?Filed Pursuant to Rule 424(b)(4)? ?Registration No. 333-257781? PROSPECTUS 1,000,000 Shares COMMON STOCK This is the initial public offering of common stock of Orange County Bancorp, Inc., the holding company for Orange Bank & Trust Company, a New York state-chartered trust company headquartered in Middletown, New York and Hudson Valley Investment Advisors, Inc., a registered in

August 4, 2021 8-A12B

Form 8-A, filed with the SEC on August 4, 2021

8-A12B 1 form8a080421.htm ORANGE COUNTY BANCORP, INC. FORM 8-A AUGUST 4, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 Orange County Bancorp, Inc. (Exact Name of Registrant as Specified in Its Charter) Delaware 26-1135778 (State or other

August 4, 2021 S-1MEF

As filed with the Securities and Exchange Commission on August 4, 2021

As filed with the Securities and Exchange Commission on August 4, 2021 Registration No.

August 3, 2021 CORRESP

[ORANGE COUNTY BANCORP, INC. LETTERHEAD]

CORRESP 1 filename1.htm [ORANGE COUNTY BANCORP, INC. LETTERHEAD] August 3, 2021 Via Edgar Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Orange County Bancorp, Inc. Registration Statement on Form S-1 (Registration Number 333-257781) Request for Acceleration of Effectiveness Ladies and Gentlemen: Reference is made to our letter, filed as correspondence via EDGAR on

August 2, 2021 CORRESP

August 2, 2021

1251 AVENUE OF THE AMERICAS, 6TH FLOOR NEW YORK, NY 10020 P 212 466-7800 | TF 800 635-6851 Piper Sandler & Co.

August 2, 2021 CORRESP

[ORANGE COUNTY BANCORP, INC. LETTERHEAD]

[ORANGE COUNTY BANCORP, INC. LETTERHEAD] August 2, 2021 Via Edgar Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Orange County Bancorp, Inc. Registration Statement on Form S-1 (Registration Number 333-257718) Request for Acceleration of Effectiveness Ladies and Gentlemen: Orange County Bancorp, Inc., a Delaware corporation (the ?Company?), hereby requests that the

July 29, 2021 S-1/A

As filed with the United States Securities and Exchange Commission on July 29, 2021.

TABLE OF CONTENTS As filed with the United States Securities and Exchange Commission on July 29, 2021.

July 29, 2021 FWP

INVESTOR Presentation July/August 2021 Safe Harbor Statement and Disclaimer Notice to and Undertaking by Recipients Orange County Bancorp, Inc. (“Orange,” the “Bank,” the “Company,” “we” or “us”) has filed a registration statement on Form S - 1 ( inc

Free Writing Prospectus Filed Pursuant to Rule 433 Registration Statement: 333-257781 Dated July 29, 2021 INVESTOR Presentation July/August 2021 Safe Harbor Statement and Disclaimer Notice to and Undertaking by Recipients Orange County Bancorp, Inc.

July 22, 2021 EX-1.1

Underwriting Agreement

Exhibit 1.1 ORANGE COUNTY Bancorp, Inc. [?] Shares of Common Stock $0.50 Par Value Per Share Underwriting Agreement [?], 2021 PIPER SANDLER & CO. 1251 Avenue of the Americas, 6th Floor New York, New York 10022 as representative of the Underwriters names in Schedule I hereto. Ladies and Gentlemen: Orange County Bancorp, Inc., a Delaware corporation (the ?Company?), the holding company for Orange Ba

July 22, 2021 CORRESP

LUSE GORMAN, PC ATTORNEYS AT LAW 5335 WISCONSIN AVENUE, N.W., SUITE 780 WASHINGTON, D.C. 20015 TELEPHONE (202) 274-2000 FACSIMILE (202) 362-2902

LUSE GORMAN, PC ATTORNEYS AT LAW 5335 WISCONSIN AVENUE, N.W., SUITE 780 WASHINGTON, D.C. 20015 TELEPHONE (202) 274-2000 FACSIMILE (202) 362-2902 www.luselaw.com WRITER?S DIRECT DIAL NUMBER WRITER?S E-MAIL (202) 274-2010 [email protected] July 22, 2021 Eric Envall, Staff Attorney U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, DC 20549-0303 Re: Orange County Bancorp, Inc. Re

July 22, 2021 S-1/A

As filed with the United States Securities and Exchange Commission on July 22, 2021.

TABLE OF CONTENTS As filed with the United States Securities and Exchange Commission on July 22, 2021.

July 9, 2021 EX-10.10

Orange County Bancorp, Inc. 2019 Equity Incentive Plan (incorporated by reference to Exhibit 10.10 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021)+

Exhibit 10.10 ORANGE COUNTY BANCORP, INC. 2019 EQUITY INCENTIVE PLAN Article 1. PURPOSE AND GENERAL PROVISIONS 1.1 Establishment of Plan. Orange County Bancorp, Inc., a Delaware corporation (the ?Company?), hereby establishes a stock incentive compensation plan known as the ?Orange County Bancorp, Inc. 2019 Equity Incentive Plan? (the ?Plan?), as set forth in this document. 1.2 Purpose of Plan. Th

July 9, 2021 EX-10.13

Orange County Trust Company Deferred Compensation Plan*

Exhibit 10.13 ORANGE COUNTY TRUST COMPANY DEFERRED COMPENSATION PLAN Purpose The purpose of this Orange County Trust Company Deferred Compensation Plan (the ?Plan?) is to provide a deferred compensation opportunity to eligible officers and members of the Board of Directors of Orange County Trust Company (the ?Bank?). The Plan is intended to be unfunded for tax purposes and to comply with the requi

July 9, 2021 EX-10.3

Employment Agreement by and between Orange Bank & Trust Company and John P. Bartolotta, effective as of January 1, 2018*

Exhibit 10.3 EXECUTION COPY EMPLOYMENT AGREEMENT This Employment Agreement (the "Agreement") is made and entered into, effective as of January 1, 2018 (the "Effective Date"), by and between Orange Bank & Trust Company (the "Bank") and John Bartolotta ("Executive"). Any reference to the "Company" shall mean Orange County Bancorp, Inc. or any successor thereto. WHEREAS, the Bank wishes to assure its

July 9, 2021 EX-21

Subsidiaries of Orange County Bancorp, Inc.*

EX-21 19 tm2116829d4ex21.htm EXHIBIT 21 Exhibit 21 Subsidiaries of the Registrant The following is a list of the subsidiaries of Orange County Bancorp, Inc.: Name State of Incorporation Orange Bank & Trust Company New York Hudson Valley Investment Advisors, Inc. New York

July 9, 2021 EX-4.1

Form of Common Stock Certificate of Orange County Bancorp, Inc. (incorporated by reference to Exhibit 4.1 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021

Exhibit 4.1 Orange County Bancorp, Inc.INCORPORATED UNDER THE LAWS OF THE STATE OF DELAWARECUSIP: 68417L 10 7 SEE REVERSE FOR CERTAIN DEFINITIONSTHIS CERTIFIES thatis the owner ofFULLY PAID AND NON-ASSESSABLE SHARES OF COMMON STOCK, PAR VALUE $0.50 PER SHARE OF Orange County Bancorp, Inc.transferable only on the books of the Corporation by the holder hereof in person or by Attorney upon surrender

July 9, 2021 EX-4.2

Form of 4.25% Fixed-to-Floating Rate Subordinated Note due 2030 of Orange County Bancorp, Inc. (incorporated by reference to Exhibit 4.2 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021)

Exhibit 4.2 ORANGE COUNTY BANCORP, INC. FORM OF 4.25% FIXED TO FLOATING RATE SUBORDINATED NOTE DUE SEPTEMBER 30, 2030 THE INDEBTEDNESS EVIDENCED BY THIS SUBORDINATED NOTE IS NOT A DEPOSIT AND IS NOT INSURED BY THE FEDERAL DEPOSIT INSURANCE CORPORATION OR ANY OTHER GOVERNMENT AGENCY OR FUND. THE INDEBTEDNESS EVIDENCED BY THIS SUBORDINATED NOTE IS SUBORDINATED AND JUNIOR IN RIGHT OF PAYMENT TO SENIO

July 9, 2021 EX-3.1

Certificate of Incorporation of Orange County Bancorp, Inc. (incorporated by reference to Exhibit 3.1 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021)

Exhibit 3.1 AMENDED AND RESTATED Certificate of Incorporation of Orange County Bancorp, Inc. The Undersigned, for the purpose of organizing a corporation pursuant to Section 102 of the Delaware General Corporation Law, does hereby certify that the Certificate of Incorporation of Orange County Bancorp, Inc. was duly adopted in accordance with the provisions of Section 102 of the Delaware General Co

July 9, 2021 EX-10.7

Participation Agreement under the Orange Bank & Trust Company Performance-Based Supplemental Executive Retirement Plan for John P. Bartolotta*

Exhibit 10.7 PARTICIPATION AGREEMENT UNDER THE ORANGE BANK & TRUST COMPANY PERFORMANCE-BASED SUPPLEMENTAL EXECUTIVE RETIREMENT PLAN THIS PARTICIPATION AGREEMENT is effective as of January 1, 2018 by and between ORANGE BANK & TRUST COMPANY (the ?Employer?), and John Bartolotta, an executive of the Employer (referred to herein as the ?Participant? and the ?Executive?) (the ?Participation Agreement?)

July 9, 2021 EX-10.6

Participation Agreement under the Orange Bank & Trust Company Performance-Based Supplemental Executive Retirement Plan for Joseph A. Ruhl (incorporated by reference to Exhibit 10.6 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021)+

Exhibit 10.6 PARTICIPATION AGREEMENT UNDER THE ORANGE BANK & TRUST COMPANY PERFORMANCE-BASED SUPPLEMENTAL EXECUTIVE RETIREMENT PLAN THIS PARTICIPATION AGREEMENT is effective as of January 1, 2018 by and between ORANGE BANK & TRUST COMPANY (the ?Employer?), and Joseph Ruhl, an executive of the Employer (referred to herein as the ?Participant? and the ?Executive?) (the ?Participation Agreement?). RE

July 9, 2021 EX-10.9

Orange Bank & Trust Company Annual Incentive Plan (incorporated by reference to Exhibit 10.9 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021) +

Exhibit 10.9 ORANGE BANK & TRUST COMPANY ANNUAL INCENTIVE PLAN Introduction and Objectives The Orange Bank & Trust Company Annual Incentive Plan (?AIP? or ?Plan?) is designed to recognize and reward management for their collective and individual contributions to the success of Orange Bank & Trust Company (the ?Bank?) and its affiliates. The Plan focuses on performance measures that are critical to

July 9, 2021 EX-3.2

Bylaws of Orange County Bancorp, Inc. (incorporated by reference to Exhibit 3.2 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021)

Exhibit 3.2 BYLAWS OF ORANGE COUNTY BANCORP, INC. ARTICLE I OFFICES Section 1. Registered Office. The registered office of Orange County Bancorp, Inc. (the "Corporation") in the State of Delaware shall be in the City of Wilmington, County of New Castle. Section 2. Other Offices. The Corporation may also have offices at such other places both within and without the State of Delaware as the Board of

July 9, 2021 S-1

Power of Attorney*

TABLE OF CONTENTS As filed with the United States Securities and Exchange Commission on July 9, 2021.

July 9, 2021 EX-10.1

Employment Agreement by and between Orange County Bancorp, Inc., Orange Bank & Trust Company and Michael J. Gilfeather, effective as of December 31, 2018*

Exhibit 10.1 EMPLOYMENT AGREEMENT This Employment Agreement (the "Agreement") is made and entered into, effective as of December 31, 2018 (the "Effective Date"), by and between Orange County Bancorp, Inc., a Delaware corporation (the "Company"), Orange Bank & Trust Company, a wholly-owned subsidiary of the Company (the "Bank") and Michael J. Gilfeather ("Executive"). Any reference to the "Employer

July 9, 2021 EX-10.12

Orange County Bancorp, Inc. Stock-Based Deferral Plan (incorporated by reference to Exhibit 10.12 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021)+

Exhibit 10.12 ORANGE COUNTY BANCORP, INC. STOCK-BASED DEFERRAL PLAN, AS AMENDED AND RESTATED 1. Purpose. The Orange County Bancorp, Inc. Stock-Based Deferral Plan provides members of the Board of Directors of the Company and its affiliates, including Orange Bank & Trust Company (?Bank?), as well as key executives of the Company and the Bank (the ?Executives?), with the opportunity to elect to defe

July 9, 2021 EX-10.11

Form of Subordinated Note Purchase Agreement, dated as of September 24, 2020, by and between Orange County Bancorp, Inc. and the several Purchasers (incorporated by reference to Exhibit 10.11 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021)

EX-10.11 16 tm2116829d4ex10-11.htm EXHIBIT 10.11 Exhibit 10.11 FORM OF SUBORDINATED NOTE PURCHASE AGREEMENT This SUBORDINATED NOTE PURCHASE AGREEMENT (this “Agreement”) is dated as of September 24, 2020, and is made by and among Orange County Bancorp, Inc., a Delaware corporation (the “Company”), and the several purchasers of the Subordinated Notes (as defined herein) identified on the signature p

July 9, 2021 EX-10.2

Employment Agreement by and between Orange Bank & Trust Company and Joseph A. Ruhl, effective as of January 1, 2018*

Exhibit 10.2 EMPLOYMENT AGREEMENT This Employment Agreement (the "Agreement") is made and entered into, effective as of January 1, 2018 (the "Effective Date"), by and between Orange Bank & Trust Company (the "Bank") and Joseph Ruhl ("Executive"). Any reference to the "Company" shall mean Orange County Bancorp, Inc. or any successor thereto. WHEREAS, the Bank wishes to assure itself of the continue

July 9, 2021 EX-10.4

Orange Bank & Trust Company Performance-Based Supplemental Executive Retirement Plan (incorporated by reference to Exhibit 10.4 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021)+

Exhibit 10.4 ORANGE BANK & TRUST COMPANY PERFORMANCE-BASED SUPPLEMENTAL EXECUTIVE RETIREMENT PLAN ARTICLE I GENERAL 1.1 PURPOSE OF THE PLAN. The purpose of the Orange Bank & Trust Company Performance-Based Supplemental Executive Retirement Plan (the ?Plan?) is to assist the Employer and its affiliates in retaining, attracting and providing supplemental executive retirement benefits to certain key

July 9, 2021 EX-10.8

Orange Bank & Trust Company Supplemental Executive Retirement Plan for Michael J. Gilfeather (incorporated by reference to Exhibit 10.8 to the Registration Statement on Form S-1 of Orange County Bancorp, Inc. (File No. 333-257781), initially filed with the Securities and Exchange Commission on July 9, 2021)+

Exhibit 10.8 ORANGE COUNTY TRUST COMPANY Supplemental Executive Retirement Plan For MICHAEL J. GILFEATHER TABLE OF CONTENTS Article I. DEFINITIONS I Article II. ELIGIBILITY AND VESTING 3 Article III. RETIREMENT BENEFIT 3 Article IV. TIME AND FORM OF PAYMENT OF THE RETIREMENT BENEFIT 4 Article V. CHANGE IN CONTROL 4 Article VI. REGULATORY PROVISIONS THAT MAY AFFECT EXECUTIVE'S RETIREMENT BENEFIT 5

July 9, 2021 EX-10.5

Participation Agreement under the Orange Bank & Trust Company Performance-Based Supplemental Executive Retirement Plan for Michael J. Gilfeather*

Exhibit 10.5 PARTICIPATION AGREEMENT UNDER THE ORANGE BANK & TRUST COMPANY PERFORMANCE-BASED SUPPLEMENTAL EXECUTIVE RETIREMENT PLAN THIS PARTICIPATION AGREEMENT is effective as of December 31, 2018 by and between ORANGE BANK & TRUST COMPANY (the ?Bank?), and MICHAEL GILFEATHER, an executive of Orange County Bancorp, Inc. (the ?Company?) and the Bank (referred to herein as the ?Participant? and the

July 8, 2021 CORRESP

LUSE GORMAN, PC ATTORNEYS AT LAW 5335 WISCONSIN AVENUE, N.W., SUITE 780 WASHINGTON, D.C. 20015 TELEPHONE (202) 274-2000 FACSIMILE (202) 362-2902

LUSE GORMAN, PC ATTORNEYS AT LAW 5335 WISCONSIN AVENUE, N.W., SUITE 780 WASHINGTON, D.C. 20015 TELEPHONE (202) 274-2000 FACSIMILE (202) 362-2902 www.luselaw.com WRITER?S DIRECT DIAL NUMBER WRITER?S E-MAIL (202) 274-2010 [email protected] July 9, 2021 Eric Envall, Staff Attorney U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, DC 20549-0303 Re: Orange County Bancorp, Inc. Reg

May 28, 2021 DRS

As confidentially submitted to the United States Securities and Exchange Commission on May 28, 2021. This draft registration statement has not been publicly filed with the United States Securities and Exchange Commission and all information herein re

TABLE OF CONTENTS As confidentially submitted to the United States Securities and Exchange Commission on May 28, 2021.

May 28, 2021 EX-10.11

FORM OF SUBORDINATED NOTE PURCHASE AGREEMENT

Exhibit 10.11 FORM OF SUBORDINATED NOTE PURCHASE AGREEMENT This SUBORDINATED NOTE PURCHASE AGREEMENT (this ?Agreement?) is dated as of September 24, 2020, and is made by and among Orange County Bancorp, Inc., a Delaware corporation (the ?Company?), and the several purchasers of the Subordinated Notes (as defined herein) identified on the signature pages hereto (each a ?Purchaser? and collectively,

May 28, 2021 EX-10.8

ORANGE COUNTY TRUST COMPANY Supplemental Executive Retirement Plan For MICHAEL J. GILFEATHER TABLE OF CONTENTS

Exhibit 10.8 ORANGE COUNTY TRUST COMPANY Supplemental Executive Retirement Plan For MICHAEL J. GILFEATHER TABLE OF CONTENTS Article I. DEFINITIONS I Article II. ELIGIBILITY AND VESTING 3 Article III. RETIREMENT BENEFIT 3 Article IV. TIME AND FORM OF PAYMENT OF THE RETIREMENT BENEFIT 4 Article V. CHANGE IN CONTROL 4 Article VI. REGULATORY PROVISIONS THAT MAY AFFECT EXECUTIVE'S RETIREMENT BENEFIT 5

May 28, 2021 EX-10.6

PARTICIPATION AGREEMENT UNDER THE ORANGE BANK & TRUST COMPANY PERFORMANCE-BASED SUPPLEMENTAL EXECUTIVE RETIREMENT PLAN

Exhibit 10.6 PARTICIPATION AGREEMENT UNDER THE ORANGE BANK & TRUST COMPANY PERFORMANCE-BASED SUPPLEMENTAL EXECUTIVE RETIREMENT PLAN THIS PARTICIPATION AGREEMENT is effective as of January 1, 2018 by and between ORANGE BANK & TRUST COMPANY (the ?Employer?), and Joseph Ruhl, an executive of the Employer (referred to herein as the ?Participant? and the ?Executive?) (the ?Participation Agreement?). RE

May 28, 2021 EX-10.9

ORANGE BANK & TRUST COMPANY ANNUAL INCENTIVE PLAN

Exhibit 10.9 ORANGE BANK & TRUST COMPANY ANNUAL INCENTIVE PLAN Introduction and Objectives The Orange Bank & Trust Company Annual Incentive Plan (?AIP? or ?Plan?) is designed to recognize and reward management for their collective and individual contributions to the success of Orange Bank & Trust Company (the ?Bank?) and its affiliates. The Plan focuses on performance measures that are critical to

May 28, 2021 EX-3.1

AMENDED AND RESTATED Certificate of Incorporation of Orange County Bancorp, Inc.

Exhibit 3.1 AMENDED AND RESTATED Certificate of Incorporation of Orange County Bancorp, Inc. The Undersigned, for the purpose of organizing a corporation pursuant to Section 102 of the Delaware General Corporation Law, does hereby certify that the Certificate of Incorporation of Orange County Bancorp, Inc. was duly adopted in accordance with the provisions of Section 102 of the Delaware General Co

May 28, 2021 EX-10.2

EXECUTION COPY EMPLOYMENT AGREEMENT

Exhibit 10.2 EXECUTION COPY EMPLOYMENT AGREEMENT This Employment Agreement (the "Agreement") is made and entered into, effective as of January 1, 2018 (the "Effective Date"), by and between Orange Bank & Trust Company (the "Bank") and Joseph Ruhl ("Executive"). Any reference to the "Company" shall mean Orange County Bancorp, Inc. or any successor thereto. WHEREAS, the Bank wishes to assure itself

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