DEF 14A of Orange County Bancorp, Inc. /DE/, Apr 15, 2026

DEF 14A of Orange County Bancorp, Inc. /DE/

Filed Apr 15, 2026 · FY20250001104659-26-043778

Open on EDGAR

  1. PROPOSAL I — ELECTION OF DIRECTORS

    PROPOSAL I — ELECTION OF DIRECTORS Our Board of Directors is comprised of nine members. Our Bylaws provide that directors are divided into three classes as nearly equal in number as possible, with one class of directors elected annually. Three directors have been nominated for election at the annual meeting. The Board of Directors has nominated Michael J. Gilfeather, Marianna R. Kennedy and Richard B. Rowley, each to serve as a director for a three-year term and until each of their respective successors shall have been elected and qualified. Messrs. Gilfeather and Rowley and Ms. Kennedy are currently directors of the Company, and each nominee has agreed to serve as a director if elected. The following sets forth certain information regarding the nominees, the other current members of our Board of Directors, and executive officers who are not directors. It is intended that the proxies solicited on behalf of the Board of Directors (other than proxies in which the vote is withheld as to any nominee) will be voted at the annual meeting for the election of the proposed nominees. If a nominee is unable to serve, the shares represented by all such proxies will be voted for the election of such substitute as the Board of Directors may determine. At this time, the Board of Directors knows of no reason why any of the nominees might be unable to serve, if elected. Except as indicated herein, there are no arrangements or understandings between any nominee or continuing director and any other person pursuant to which such nominee or continuing director was selected. Age information is as of March 30, 2026, and term as a director includes service with Orange Bank & Trust Company (the “Bank”) prior to the incorporation of the Company.

  2. Directors

    Directors The nominees for director for a term ending in 2029 are: Michael J. Gilfeather. Mr. Gilfeather has been President and Chief Executive Officer of the Company and the Bank since April 2014. Mr. Gilfeather also serves as a director of the Company, the Bank and Orange Investment Advisors, Inc. (“OIA”). Mr. Gilfeather began his banking career with The Bank of New York and was the Division Head responsible for all retail banking in Manhattan for 10 years. He was later an Executive Vice President and Chief Administrative Officer at Hudson Valley Bank overseeing all Branch Banking, Trust and Human Resources. In 2026, Mr. Gilfeather was appointed to the Board of Directors of the Federal Reserve Bank of New York as a Class A Director, representing member banks of the Second Federal Reserve District with capital and surplus between $40 million and $2 billion. Mr. Gilfeather’s other outside board responsibility is with the New York Bankers Association where he is a past Chairman and serves on the Executive Committee. He was most recently on the Executive Board and prior Chairman of the Orange County Partnership, an economic development organization. In addition, he was previously on the boards of the Orange Regional Hospital Foundation, the Orange County Chamber of Commerce and the United Way of Orange & Dutchess Counties. Mr. Gilfeather has a Bachelor of Science degree in Psychology from Union College and a Master of Business Administration degree from Pace University. Mr. Gilfeather’s extensive knowledge of the banking industry and strong leadership skills provide the Board with invaluable insight and guidance into the business and regulatory requirements of today’s banking environment. Age 68. Director since 2014. Marianna R. Kennedy. Ms. Kennedy is a practicing attorney and partner at Drake Loeb PLLC, a distinguished law firm in the Hudson Valley. She has concentrated her practice on business and financial transactions. She represents regional and national businesses primarily in matters involving acquisitions, sales and mergers, commercial contracts, succession planning, commercial borrowing, and leasing. Ms. Kennedy is a current and past member of numerous boards, many of which she served in leadership positions. Ms. Kennedy graduated magna cum laude from Pace University School of Law. Ms. Kennedy’s experience as a partner in a law firm, and her transactional experience and involvement in business and civic organizations in the communities served by the Company and its affiliates, provide the Board of Directors of the Company with valuable insight. Age 62. Director since 2022. Richard B. Rowley. Mr. Rowley is President of Libertyville Capital Group and Rowley Development Corp. Mr. Rowley is also the former CEO and owner of Rowley Building Products and Window Tech. Mr. Rowley also serves as the Chairman of OIA. He has a Bachelor of Arts degree from Susquehanna University and Diplomas in British History, Politics, and Fine Arts from University College, Oxford England. Mr. Rowley is a prominent regional philanthropist whose accomplishments include the Rowley Birthing Center at Garnet Health Medical Center and the Rowley Engineering and Science Building on the Middletown Campus of Orange County Community College. Mr. Rowley is a current and past member of numerous boards, many of which he served in leadership positions. Mr. Rowley’s extensive business experience and community involvement provides the Board of Directors of the Company and its affiliates with insight into the economic and business trends in our market area. Age 71. Director since 2009. The Board of Directors recommends a vote “FOR” each of the nominees for director. The following directors have terms ending in 2027: Gregory F. Holcombe. Mr. Holcombe is a builder, owner and manager of multi-family and mixed-use properties in lower Westchester County, New York. From 1995 to 2006, Mr. Holcombe served as Vice President of Supply Chain Development for Precision Valve Corporation. Mr. Holcombe served as a director of Hudson Valley Holding Corp. and Hudson Valley Bank from 1999 to 2015. Mr. Holcombe received a Bachelor of Arts degree in Latin American Studies and International Marketing from Tulane University and has served and continues to serve on the boards of directors of several corporate and community organizations. Mr. Holcombe’s prior bank board service, along with his skills in driving company performance and knowledge of our local community will assist us as we continue to grow. Age 64. Director since 2017. Jonathan Schiller. Mr. Schiller is an entrepreneur with vast senior leadership experience. He is the President and CEO of Hospicom Inc., a world-class medical education and consulting company that serves Fortune 100 pharmaceutical and biotechnology companies. Mr. Schiller founded Hospicom Inc. in 2003 and successfully led Hospicom’s transition from a startup to a highly successful, multimillion-dollar global organization. He previously founded the Society of Academic Medicine and Strategically Speaking Inc. Mr. Schiller earned a BS in Pharmacy and is a Registered Pharmacist from St. John’s University and an MBA in Marketing / Marketing Management from Columbia University Business School. Mr. Schiller’s consulting experience, along with his skills in driving company performance are valuable assets to the board. Age 61. Director since 2024. Olga Luz Tirado. Ms. Tirado is the President of O Communications & Solutions, LLC, a minority- and women-owned public relations and branding agency she founded in 2017. She previously spent a decade leading The Bronx Tourism Council, where she spearheaded successful campaigns that connected cultural institutions, restaurants, businesses, and corporate partners, while helping to rebrand the borough, highlighting its rich history and diversity to both domestic and global audiences. During her tenure, Ms. Tirado managed high-profile events including Bronx Week, Tour de Bronx, and Savor the Bronx Restaurant Week. She also published the first-ever Annual Bronx Visitor Guide and produced and hosted the Webby Award winning podcast, Go Bronx Pod. Ms. Tirado serves on the Board of Directors of the New York State Tourism Industry Association, where she chairs the Diversity, Equity, Inclusion, and Accessibility Committee. In 2026, she was also appointed to the Hudson Valley Regional Council. Her deep involvement in business and civic organizations across the Bronx and New York City provides valuable insight into emerging and expanding market opportunities. Age 65. Director since 2023. The following directors have terms ending in 2028: Kevin J. Keane. Mr. Keane is the Managing Partner for PKF O’Connor Davies, the nation’s 26th largest accounting and advisory firm. With more than 30 years’ experience, Mr. Keane is recognized for delivering outstanding accounting and business advisory services and exceptional client experiences to the high-net-worth and family-owned companies in the manufacturing, distribution, real estate, construction industries and more. Mr. Keane is a supporter of various charities and an active participant on boards of directors and finance committees for many area nonprofit organizations and clubs, including the John A. Coleman School of the Elizabeth Seton Pediatric Center, Lititz Watch Technicum and the Irish Arts Center. He is also the Chairman of the Board of Trustees for his alma mater, Archbishop Stepinac High School. Mr. Keane was a founder of The Westchester Bank and served on the board of directors of the bank until the bank was acquired in 2021. Mr. Keane is a graduate of the State University of New York at Albany and earned his Master of Business Administration degree in corporate finance from Pace University. Mr. Keane’s expertise

  3. Directors

    in accounting and business advisory services as well as his local and regional community involvement are valuable assets to the Board of Directors of the Company. Age 69. Director since 2022. William D. Morrison. Mr. Morrison is an independent insurance professional and served for 23 years as a senior account executive in commercial insurance with Marshall & Sterling Insurance Company. He has a Bachelor of Science in Business Administration degree from Marist College. Mr. Morrison is a current or past board member of several community, corporate and charitable organizations. Mr. Morrison’s work experience provides the Board of Directors of the Company with strong insight into budgeting and financial strategy. Age 71. Director since 2004. Jonathan F. Rouis, CPA. Mr. Rouis serves as our Chairman of the Board. Mr. Rouis is a Partner at RBT CPAs, an accounting, auditing, tax and consulting firm and the former managing partner at Rouis & Company LLC CPAs. Mr. Rouis served on the Sullivan County Legislature and served as its Chairman. He has a Bachelor of Business Administration degree in Accounting from St. Bonaventure University. Mr. Rouis is a member or past member of several professional and community organizations, including serving on the Greater Hudson Valley Health Systems board of directors. Mr. Rouis’ expertise in accounting and corporate management and his community involvement are valuable assets to the board. Age 54. Director since 2018.

  4. Executive Officers Who are Not Directors

    Executive Officers Who are Not Directors Joseph A. Ruhl. Mr. Ruhl joined the Bank in 2015 to lead the commercial business expansion into Westchester County as Executive Vice President, Regional President for Westchester and Chief Deposit Officer. In 2026, Mr. Ruhl was promoted to Senior Executive Vice President recognizing his leadership, performance, and contributions to the Bank’s growth in the Westchester County and Lower Hudson Valley markets. Mr. Ruhl spent the first part of his career as a practicing attorney until joining Hudson Valley Bank over 25 years ago as First Senior Vice President and Division Executive in charge of its Legal Services Division. Mr. Ruhl has a Juris Doctor from Pace University School of Law and a Bachelor of Arts from Fordham University. Mr. Ruhl is active in many civic and charitable causes in the Company’s market area. Mr. Ruhl is the Chairman Emeritus of the Board of the St. Philip the Apostle Foundation, and the Secretary of the Italian American Forum. Mr. Ruhl is an active member of various bar associations, a Director of the Columbian Lawyers Association of Westchester County, and a frequent lecturer on business management, ethics and attorney banking issues. Age 60. Michael Lesler. Mr. Lesler joined the Company and Bank in December 2021 as Senior Vice President, Controller and Chief Accounting Officer. He was promoted to Senior Vice President and Chief Financial Officer in March 2023 and named Executive Vice President and Chief Financial Officer in December 2023 adding responsibility for oversight of the Bank’s Information Technology Department. Mr. Lesler has over 20 years of experience in the banking industry. Prior to joining the Company and the Bank, Mr. Lesler served as Executive Vice President and Chief Operating Officer for BCB Bancorp, Inc. from 2018 to 2021 and prior to that, he served in the same position at Clifton Bancorp, Inc. from 2016 to 2018. He also held the positions of Chief Financial Officer and President and Chief Executive Officer at Bank of New Jersey where he served for 11 years. Mr. Lesler currently serves on the Boards of Garnet Health Foundation, United Way of Orange & Dutchess Counties and the Clifton Boys & Girls Club. Mr. Lesler holds a Bachelor of Science degree in accounting from Rutgers University. Age 55. Gregory Sousa. Mr. Sousa joined the Bank in 2015 as Vice President and Senior Relationship Manager developing deposit and lending businesses as the Bank built out its Rockland and Westchester markets. In 2017, he was promoted to First Vice President and given the added responsibility of leading business development efforts for all Orange and Rockland branches. In recognition of his impact on both fronts, he was promoted to Senior Vice President in 2018, adding responsibility for Marketing and Product Development initiatives to his portfolio. In 2020, Mr. Sousa was promoted to Executive Vice President, Chief Commercial Banking Officer, and in 2023 he was named Deputy Chief Lending Officer. In July 2024, Mr. Sousa was promoted to Executive Vice President, Chief Lending Officer. Mr. Sousa has over 20 years of experience in the banking industry. Prior to joining the Bank, Mr. Sousa previously worked at Union State Bank and TD/Commerce Bank. Mr. Sousa has a Bachelor’s degree in Economics from the State University of New York at Binghamton. Mr. Sousa has also been recognized as one of Rockland County’s “Forty Under 40,” is a graduate of Leadership Rockland and a graduate of ABA Stonier Graduate School of Banking, earning his Wharton Leadership Certificate in 2015. Age 46. Orville Aarons. Mr. Aarons joined the Bank in October 2025 as Executive Vice President and Chief of Credit Risk Management. In this role, Mr. Aarons is responsible for institutional portfolio management and underwriting support for the Bank’s top commercial borrowers. He oversees the Bank’s Credit Department and manages the participation loan portfolio, ensuring rigorous credit discipline. Prior to joining the Bank, Mr. Aarons worked with various financial institutions through his consulting firm, O. Aarons & Company, Inc., that was established in 1992. Through his firm, he served as interim management and provided investment banking services primarily to financial institutions, principal groups and middle-market operating companies. Mr. Aarons brings decades of senior-level banking experience, most recently serving as President and a Director for Catskill Hudson Bank, previously as Director of Naugatuck Valley Financial Corporation and Executive Vice President and Chief Lending Officer for The Community’s Bank. He has also held leadership roles at National Westminster Bank. Mr. Aarons holds a Bachelor’s degree from Georgetown University and a Master of Business Administration degree from the University of Chicago. Age 72. David P. Dineen. Mr. Dineen joined the Company in March 2022 as the Senior Vice President, Director of Wealth Services. Mr. Dineen was promoted to Executive Vice President / Senior Managing Director of Wealth Services in January 2025. Mr. Dineen oversees the Company’s Orange Wealth Management Program which consists of investment services provided through OIA and trust and private banking services provided through the Bank. Mr. Dineen has over 35 years of experience in the banking industry. Prior to joining the Bank, Mr. Dineen previously worked at Republic Bank, Bankwell Financial, The Bank of New York, Commerce Bank, North Fork Bank, and Capital One. Mr. Dineen most recently served as Senior Vice President, Market Manager at Republic Bank from 2019 to 2021, where he was responsible for treasury management, lending, and establishment of their Private Banking group. Prior to that Mr. Dineen previously served as Executive Vice President, Community Banking Officer at Bankwell Financial from 2016 to 2019, where he was part of the executive team responsible for 12 branch offices, training, deposit operations and treasury management. Mr. Dineen has a Bachelor of Business Administration degree from Saint Joseph’s College. Age 62. Elizabeth Jones. Ms. Jones joined the Bank in 2016 as First Vice President, Director of Branch and Deposit Operations. In 2018, she was given the responsibility of Loan Operations, and in 2021, she was promoted to Director of Operations. In 2022, Ms. Jones was appointed Senior Vice President, Chief Operating Officer and in 2025, Ms. Jones was promoted to Executive Vice President. In this role, Ms. Jones oversees all branch operations, deposit operations, loan operations, compliance, project management, and facilities. Ms. Jones has over 20 years of experience in the banking industry. Prior to joining the Bank, Ms. Jones worked at Sterling National Bank, where she served in various operational roles during her 20-year tenure. Age 47. Michael Listner. Mr. Listner joined the Bank in 2018 as First Vice President and Senior Credit Officer and was promoted to Senior Vice President and Chief Credit Officer of the Bank 2020. Mr. Listner became Senior Vice President and Chief Risk Officer in March 2023. Prior to joining the Bank, Mr. Listner previously worked at Sun National Bank and BBVA Compass Bank. Prior to his roles in the banking industry, Mr. Listner worked at Standard & Poor’s, covering structured finance products and both investment grade and high yield corporates. Mr. Listner has a Master of Business Administration degree in finance and accounting from New York University Stern School of Business and a Bachelor of Science degree in finance and economics from Villanova University. Age 48.

  5. Executive Officers Who are Not Directors

    Stephen Rooney. Mr. Rooney joined the Bank in August 2022 and currently serves as Senior Vice President, Chief Credit Officer. Mr. Rooney has over 35 years of experience in the banking industry. From 2014 to 2022, Mr. Rooney was a Senior Vice President for Unity Bank, serving as both Chief Lending Officer and Chief Credit Officer over that period. Prior to Unity Bank, Mr. Rooney held progressively more senior positions at Sun National Bank, Standard & Poor’s and Philadelphia National Bank. Mr. Rooney has a Master of Business Administration degree in Finance from New York University Stern School of Business and a Business Administration degree in Finance/Humanities from Providence College. Age 63.

  6. Summary Compensation Table

    Summary Compensation Table The following table sets forth certain information as to the total remuneration paid by the Company to our President and Chief Executive Officer, Michael J. Gilfeather, and our two other most highly compensated executive officers for the year ended December 31, 2025. Each individual listed in the table below is referred to as a “named executive officer.”

  7. Summary Compensation Table

    | Name and Principal Position | Year | Salary ($) | Bonus ($) | Stock Awards ($)(1) | Non-Equity Incentive Plan Compensation ($)(2) | Nonqualified Deferred Comp Earnings ($) | All Other Compensation ($)(5) | Total ($) | | Michael J. Gilfeather President, Chief Executive Officer and Director of the Company and the Bank | 2025 | 700,000 | ― | 609,001 | 450,000 | ― | 333,481 | 2,092,482 | | | 2024 | 670,000 | ― | 523,966 | 350,000 | ― | 348,803 | 1,892,769 | | Joseph A. Ruhl Executive Vice President and Regional President of the Bank | 2025 | 355,350 | ― | 144,908 | 200,000 | ― | 103,244 | 803,502 | | | 2024 | 345,000 | ― | 125,642 | 180,000 | ― | 102,690 | 753,332 | | Michael Lesler(3) Executive Vice President, Chief Financial Officer of the Company and the Bank | 2025 | 350,200 | 50,000(4) | 142,808 | 180,000 | ― | 59,602 | 782,610 |

  8. Summary Compensation Table

    (1) The stock awards reported in 2025 reflect the grant date fair value of the restricted stock unit awards under Accounting Standards Codification (ASC) Topic 718. Restrictions on the restricted stock unit awards lapse at the rate of 33% per year. The assumptions used to determine the value of stock awards are described in Note 1 to the Notes to the Consolidated Financial Statements in the Annual Report on Form 10-K. See also “— Incentive Compensation Plans — Equity-Based Long-Term Incentives” for additional information on the restricted stock unit awards. (2) Represents cash payments earned under the Annual Incentive Plan by each named executive officer during each year indicated. See “— Incentive Compensation Plans — Cash-Based Short-Term Incentives” for a detailed description of the Annual Incentive Plan. (3) Mr. Lesler became a named executive officer for the first time in 2025 and, pursuant to SEC rules, compensation for prior years is not required to be reported. (4) Discretionary bonus awarded in recognition of Mr. Lesler’s dedicated work and execution of 2025 capital initiatives, including the successful capital raise and refinance of the Company’s subordinated debt. (5) The amounts in this column represent all other compensation not reported in prior columns in this table, including perquisites, the aggregate value of which exceeds $10,000. This column consists of the following payments in 2025:

  9. Summary Compensation Table

    | Officer | Perquisites ($)(a) | Life Insurance ($)(b) | 401(k) ($)(c) | Performance SERP ($)(d) | Total ($) | | Michael J. Gilfeather | 21,544 | 11,687 | 40,250 | 260,000 | 333,481 | | Joseph A. Ruhl | 12,994 | ― | 40,250 | 50,000 | 103,244 | | Michael Lesler | 6,000 | ― | 18,582 | 35,020 | 59,602 |

  10. Summary Compensation Table

    (a) The value of the executive’s automobile allowance. (b) This amount represents the taxable income associated with the named executive officer’s life insurance benefit. (c) This amount represents matching and employer discretionary contributions made to the 401(k). See “Tax-Qualified Retirement Plans — 401(k) Plan.” (d) This amount represents employer contributions to each executive’s Performance-Based Supplemental Executive Retirement Plan (“Performance-Based SERP”) account.

  11. Non-Qualified Deferred Compensation Arrangements

    Non-Qualified Deferred Compensation Arrangements Gilfeather SERP. In April 2014, the Bank implemented a supplemental executive retirement plan for Mr. Gilfeather with a one-time contribution of $15,000. The Boards of Directors of the Bank and the Company may authorize additional contributions to Mr. Gilfeather’s SERP account; however, no additional contributions have been made since 2014. Mr. Gilfeather’s SERP benefit is fully vested and will be distributed in a lump sum within the earlier of 45 days following his separation from service or 30 days following a Change in Control (as defined in the Gilfeather SERP). During 2025, Mr. Gilfeather earned interest on his SERP Account balance at the rate of 2.6%. Performance-Based SERP. All of the named executive officers are participants in the Performance-Based SERP, a non-qualified deferred compensation plan that provides supplemental retirement benefits to each participating executive which may be distributed in cash or Company common stock. The Bank maintains a bookkeeping account on behalf of each of our named executive officers. All of our named executive officers have entered into participation agreements with the Bank that outline their Performance-Based SERP opportunities. During the term of his employment agreement, Mr. Gilfeather is eligible for an annual contribution of $260,000 to his Performance-Based SERP Account, if (i) he is employed by the Bank and the Company on December 31st of each applicable year, (ii) the Bank has $2.5 billion in total assets for two consecutive quarters during an applicable fiscal year, and (iii) Mr. Gilfeather satisfies at least 80% of his annual goals established for an applicable fiscal year. Mr. Gilfeather became fully vested in his Performance-Based SERP Account upon attainment of age 65. During the term of his employment agreement, Mr. Ruhl is eligible for an annual contribution of $50,000 to his Performance-Based SERP account, if: (i) he is employed by the Bank and the Company on December 31st of each applicable year and (ii) he satisfies at least 80% of his annual goals established for an applicable fiscal year. Mr. Ruhl will fully vest in his Performance-Based SERP Account upon the earlier of (i) his attainment of age 65, (ii) his attainment of age 62 with ten (10) years of service, or (iii) a change in control occurs. Under the terms of Mr. Lesler’s participation agreement, he is entitled to an employer contribution of 10% of his base salary each year he is employed by the Bank through December 31, 2026. Each employer contribution made to Mr. Lesler under the Performance-Based SERP will fully vest in his Performance-Based SERP Account upon the earlier of (i) his attainment of normal retirement age (age 62 with 10 years of service), (ii) change in control, or (iii) participant’s death. During 2025, Performance-based SERP Accounts credited in cash earned interest at the rate of 2.60%. The vested portion of each named executive officer’s Performance-Based SERP account becomes payable upon separation from service (other than for cause) and will be paid in five equal annual installments. In the event an executive’s employment is terminated within 12 months following a change in control, the Performance-Based SERP accounts will be distributed in a lump sum as soon as practicable following termination of employment. Orange Bank & Trust Company Non-Qualified Deferred Compensation Plan. The Bank maintains the Orange Bank & Trust Company Non-Qualified Deferred Compensation Plan (the “Deferred Compensation Plan”) as a vehicle for select executives to defer receipt of certain compensation earned for service with the Bank and its affiliates until separation from service (other than death), a specified date/age or death. The Deferred Compensation Plan is a non-qualified deferred compensation plan that is intended to comply with Section 409A of the Internal Revenue Code, and the “top hat pension plan” requirements of the Employee Retirement Income Security Act of 1974. Participation in the Deferred Compensation Plan is voluntary and limited to a select group of management or highly compensated employees selected by the Compensation Committee of the Board of Directors of the Bank in its sole discretion. The named executive officers are all eligible to participate in the Deferred Compensation Plan. None of the named executive officers deferred compensation under the plan in 2025. Elective deferrals are credited to participant accounts on the date a participant’s compensation would have been paid to the participant absent the deferral election. Participant accounts are not credited with earnings. Therefore, the value of an account will always equal the dollar amount a participant has deferred into the Deferred Compensation Plan and will always be 100% vested. Obligations established under the terms of the Deferred Compensation Plan are satisfied from the general assets of the Bank. To the extent that any person acquires a right to receive payments under the Deferred Compensation Plan, such rights are no greater than the right of an unsecured general creditor of the Bank. Orange County Bancorp, Inc. Stock-Based Deferral Plan, as amended and restated. Mr. Gilfeather is a participant in the Stock-Based Deferral Plan as a result of a one-time transfer from the Performance-Based SERP into the Stock-Based Deferral Plan. Mr. Gilfeather has made no further deferrals to the Stock-Based Deferral Plan. See “Director Compensation — Stock-Based Deferral Plan.”

  12. Tax-Qualified Retirement Plans

    Tax-Qualified Retirement Plans Pension Plan. The Bank maintains the New York State Bankers Retirement System Volume Submitter Plan (the “Pension Plan”), as adopted by the Bank, a tax-qualified defined benefit plan for eligible employees. An employee must have completed one year of service as well as 1,000 hours and attained age 21 to have been eligible to participate in the Pension Plan. The Pension Plan was closed to new participants and benefit accruals were frozen as of December 31, 2015. Mr. Gilfeather is the only named executive officer who is a participant in the Pension Plan. Under the Pension Plan, if a participant retires after attaining age 65, the participant may elect to receive several alternative normal retirement benefit payments ranging in various payment periods from lump sum up to 60 monthly payments. If a participant retires prior to age 65 but after attaining age 55 with five years of service, the participant will be entitled to a reduced early retirement benefit. 401(k) Plan. The Orange County Bancorp, Inc. 401(k) Plan (the “401(k)”) is a tax-qualified defined contribution plan for eligible employees of the Company, the Bank and OIA. Messrs. Gilfeather, Ruhl, and Lesler are eligible to make elective deferrals into the 401(k) under the same terms as other employees. An employee must have completed 500 hours of service in a six-month computation period and attain age 21 to be eligible to make elective deferrals into the 401(k). Participants in the 401(k) may elect to defer up to 85% of their Plan compensation, on a pre-tax and post-tax basis, up to the limit permitted by the Internal Revenue Code. If a participant does not affirmatively elect not to defer, the participant will automatically be enrolled with a deferral rate of 6%. The Bank currently provides participants with a safe harbor profit-sharing contribution to active participants in the 401(k). Additionally, the Bank may make discretionary employer profit-sharing contributions to the 401(k), which may be in the form of Company common stock. The 401(k) also provides for age-based discretionary contributions for individuals age 21 and above who were employed by the Bank before April 1, 2016. Messrs. Gilfeather and Ruhl were each eligible for an age-based discretionary contribution equal to 8.50% of their base pay subject to Internal Revenue Code limits. Participant salary deferrals, employer safe harbor contributions and employer discretionary profit-sharing contributions, including the age-based discretionary contributions are always 100% vested. For participants employed on or after April 1, 2016, the Bank matches 100% on the first 4% of pay deferred (as limited by Treasury regulations). Mr. Lesler was eligible for the matching contribution. Matching contributions vest at a rate of 33.33% per year after one year of service. See “Summary Compensation Table — All Other Compensation” for information on the contributions made to the named executive officers under the 401(k).

  13. Outstanding Equity Awards at Fiscal Year End

    Outstanding Equity Awards at Fiscal Year End The following table shows stock awards outstanding for each of our named executive officers as of December 31, 2025.

  14. Outstanding Equity Awards at Fiscal Year End

    | | | Stock Awards | | | Name | Grant Date | Number of shares or units of stock that have not vested(1) | Market value of shares or units of stock that have not vested ($)(2) | | Michael J. Gilfeather | 3/10/2023 | 3,296 | 94,101 | | | 1/23/2024 | 5,164(3) | 147,432 | | | 3/21/2024 | 11,444 | 326,726 | | | 2/14/2025 | 5,247(3) | 149,802 | | | 3/20/2025 | 19,206 | 548,331 | | Joseph A. Ruhl | 3/10/2023 | 1,274 | 36,373 | | | 3/21/2024 | 3,686 | 105,235 | | | 3/20/2025 | 5,934 | 169,416 | | Michael Lesler | 3/10/2023 | 752 | 21,470 | | | 3/21/2024 | 2,642 | 75,429 | | | 3/20/2025 | 5,848 | 166,960 |

  15. Outstanding Equity Awards at Fiscal Year End

    (1) Awards generally vest in approximately 33% increments on the first, second and third anniversary of the date of grant, and are subject to executive’s employment on the respective vesting dates. (2) Market value is calculated on the basis of $28.55 per share, which was the closing sales price for our common stock as reported on the Nasdaq Capital Market on December 31, 2025. (3) Restricted stock units vest and become payable on December 31, 2026.

  16. DIRECTOR COMPENSATION

    DIRECTOR COMPENSATION

  17. Director Compensation Table

    Director Compensation Table The following table sets forth for the fiscal year ended December 31, 2025 certain information as to the total remuneration we paid to our non-employee directors. Mr. Gilfeather does not receive any additional compensation for service on the Bank and/or Company Boards of Directors.

  18. Director Compensation Table

    | Name | Fees Earned or Paid in Cash ($)(1) | Stock Awards ($)(2) | Non-Qualified Deferred Comp | All Other Compensation ($)(3) | Total ($) | | Gregory F. Holcombe | 87,552 | 25,761 | ― | ― | 113,313 | | Kevin J. Keane | 77,252 | 25,761 | ― | ― | 103,013 | | Marianna R. Kennedy | 82,402 | 25,761 | ― | ― | 108,163 | | William D. Morrison | 98,052 | 25,761 | ― | ― | 123,813 | | Jonathan F. Rouis | 128,752 | 25,761 | ― | ― | 154,513 | | Richard B. Rowley | 103,052 | 25,761 | ― | ― | 128,813 | | Jonathan Schiller | 77,252 | 25,761 | ― | ― | 103,013 | | Olga Luz Tirado | 77,252 | 25,761 | ― | ― | 103,013 |

  19. Director Compensation Table

    (1) Non-employee directors may defer all or a portion of their fees earned in cash into the Company’s Stock-Based Deferral Plan, as amended and restated. (2) Each non-employee director receives an annual equity award in the form of time-based restricted stock units under the Company’s 2023 Equity Incentive Plan as part of their director compensation. In connection with the equity grants to non-employee directors, the compensation committee engaged AON to conduct a peer analysis and the committee has considered the data provided on its peers. To encourage directors to have a meaningful ownership stake in the Company during their tenure on the Board, the outstanding restricted stock units vest one year from the grant date. As of December 31, 2025, each directors has 995 unvested restricted stock units. Non-employee directors are permitted to defer their restricted stock unit awards under the terms of the Company’s Stock-Based Deferral Plan, as amended and restated. The amounts in this chart represent the aggregate grant date fair value for restricted stock units granted during 2025 computed in accordance with FASB ASC Topic 718. The assumptions used to determine the value of stock awards are described in Note 1 to the Notes to the Consolidated Financial Statements in the Annual Report on Form 10-K. (3) Perquisites and personal benefits for each director did not exceed in the aggregate $10,000.