Other Events Orange County Bancorp, Inc., parent company of Orange Bank & Trust Company and Orange Investment Advisors, Inc. today announced a declaration of a $0.18 cash dividend per share of its common stock. The dividend will be paid on September 15, 2026 to shareholders of record on September 4, 2026. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Other Events Orange County Bancorp, Inc., parent company of Orange Bank & Trust Company and Orange Investment Advisors, Inc. today announced a declaration of a $0.18 cash dividend per share of its common stock. The dividend will be paid on June 15, 2026 to shareholders of record on June 4, 2026. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Michael J. Gilfeather: The employment agreement and SERP Participation Agreement for the CEO were amended to extend the term and provide a discretionary employer contribution.

Other Events Orange County Bancorp, Inc., parent company of Orange Bank & Trust Company and Orange Investment Advisors, Inc. today announced a declaration of a $0.18 cash dividend per share of its common stock. The dividend will be paid on March 16, 2026 to shareholders of record on March 4, 2026. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Other Events Orange County Bancorp, Inc., parent company of Orange Bank & Trust Company and Orange Investment Advisors, Inc. today announced a $0.05 increase and a declaration of a $0.18 cash dividend per share of its common stock. The dividend will be paid on December 16, 2025 to shareholders of record on December 4, 2025. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Entry into a Material Definitive Agreement On September 25, 2025, Orange County Bancorp, Inc. (the “Company”), the holding company for Orange Bank & Trust Company, a New York trust company, entered into Subordinated Note Purchase Agreements (the “Agreements”) with certain qualified institutional buyers (the “Purchasers”) and, pursuant to the Agreements, issued to the Purchasers $25.0 million in aggregate principal amount of the Company’s 6.50% Fixed-to-Floating Rate Subordinated Notes due 203…

Creation of a Direct Financial Obligation or an Obligation Under an Off-Balance Sheet Arrangement of a Registrant The discussion under

and in Exhibit 99.1 of this Current Report on Form 8-K shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, and such information shall not be deemed incorporated by reference in any filing under the Securities Act or the Exchange Act, except as shall be expressly set forth by specific reference in such filing. Cautionary Note Regarding Forward-Looking Statements…

Director, CEO, CIO — Gustave “Gus” J. Scacco: Mr. Scacco resigned from the Board of Directors and his roles as CEO and CIO.

Other Events Orange County Bancorp, Inc., 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 shareholders of record on September 8, 2025. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Entry into a Material Definitive Agreement On June 3, 2025, Orange County Bancorp, Inc. (the “Company”) and Orange Bank & Trust Company (the “Bank”) entered into an underwriting agreement (the “Underwriting Agreement”) with Piper Sandler & Co., as representative of the underwriters named therein (the “Underwriters”). Pursuant to the terms of the Underwriting Agreement, the Company agreed to issue and sell, and the Underwriters agreed to purchase, subject to and on the conditions set forth the…

Other Events Orange County Bancorp, Inc., 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 record on June 4, 2025. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Entry into a Material Definitive Agreement On April 17, 2025, Orange Bank & Trust Company (the “Bank”), a wholly owned subsidiary of Orange County Bancorp, Inc. entered into a Sale and Purchase Agreement (the “Agreement”) with JRTN Properties LLC (the “Buyer”), to sell the building and a portion of the surrounding land at the Bank’s branch located at 33 Trust Way in Middletown, New York. The purchase price of $2,535,000 will be payable to the Bank at closing. The Bank has agreed to lease the…

Michael J. Gilfeather: The employment agreement and participation agreement were amended to extend the term and adjust performance metrics.

Other Events Orange County Bancorp, Inc., 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 shareholders of record on March 4, 2024. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Other Events On November 22, 2024, Orange County Bancorp, Inc., parent company of Orange Bank & Trust Company and Hudson Valley Investment Advisors, Inc. 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 16, 2024 to shareholders of record on December 4, 2024. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Director — Jon Schiller: Jon Schiller was appointed to the Boards of Directors of Orange County Bancorp, Inc. and Orange Bank & Trust Company.

Other Events 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 of record on September 4, 2024. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Other Events 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 on June 4, 2024. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Michael Lesler and Gregory Sousa became participants in the Change in Control Severance Plan.

Other Events 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 record on March 4, 2024. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.

Director — Louis Heimbach: Director Louis Heimbach will not stand for re-election at the next annual meeting.

President and Chief Executive Officer — Michael J. Gilfeather: Amended and restated Employment Agreement with Michael J. Gilfeather, President and Chief Executive Officer.

Director — Terry Saturno: Ms. Terry Saturno will not stand for re-election and is resigning from the Boards effective May 16, 2024.

Other Events 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 of record on December 4, 2023. A press release announcing the declaration of the cash dividend is attached as Exhibit 99.1 to this Current Report on Form 8-K.