President and Chief Executive Officer of Orange Bank & Trust Company

Jul 07, 2026

Michael J. Gilfeather

Michael J. Gilfeather is the President and Chief Executive Officer of Orange Bank & Trust Company and its holding company, Orange County Bancorp Inc. He is responsible for leading the bank’s strategic transformation into a premier business and wealth management institution serving clients across Orange, Westchester, Rockland, and Bronx counties. Under his leadership, the bank has grown to over $2.7 billion in assets.

With more than four decades of experience in financial services, Gilfeather is a visionary and results-driven leader known for his ability to reposition and grow institutions. He is deeply committed to the communities the bank serves and has championed initiatives that combine financial strength with local impact. His leadership also extends to Orange Investment Advisors, Inc. (OIA), the holding company’s asset management subsidiary.

Gilfeather began his career at The Bank of New York, where he led all retail banking operations in Manhattan. He later served as Executive Vice President and Chief Administrative Officer at Hudson Valley Bank, overseeing branch banking, trust services, and human resources.

Gilfeather has an MBA in Finance from Pace University and a Bachelor of Science in Psychology from Union College. Gilfeather serves on the Board of Directors of the Federal Reserve Bank of New York. His additional outside board responsibilities include the New York Bankers Association (served as Chairman from 2021-2023). In 2022 he concluded his chairmanship of the Orange County Partnership where he served for three years.

Gilfeather’s leadership and impact have earned him numerous accolades, including 2023 Top CEOs & Business Leaders by 914INC. Magazine, 2024 Notable Leaders in Finance by Crain's New York Business, 2024 New York Best in Banking by Forbes & Fortune, 2025 Westchester Power 100 by City & State, and 2025 Bronx Power List by Schneps Media.