MEMBERFederal Reserve SystemFederal Home Loan BankFederal Deposit Insurance Corporation SUBSIDIARIESOrange Bank and Trust Company (“Bank”)Orange Investment Advisors (“OIA”) SHARES OF ORANGE COUNTYBANCORP, INC. STOCK TRADESON THE NASDAQ STOCK MARKETUNDER THE STOCK SYMBOL OBT For information regarding stock transfersand other transactions, contactour Transfer Agent:COMPUTERSHARE, INC.150 Royall Street, Suite 101, Canton, MA 020211.800.368.5948 Orange County Bancorp, Inc. Board of Directors Orange Investment Advisors Board of Directors Pictured Above: Richard B. Rowley, Chairman,Michael J. Gilfeather,William D. Morrison David P. DineenExecutive Vice PresidentSenior Managing Director,Orange Wealth Management Greg F. HolcombePresident & CEOHolcombe Development Companies Olga Luz TiradoPresident Letter from the Chairman and President The last several years have brought significant challenges to the banking industry. Volatile interestrates, economic and geopolitical uncertainties, and an ever-evolving regulatory environment have allcontributed to a less-than-ideal operating environment for the historically measured and deliberatebanking industry. Orange County Bancorp hasn’t been immune to these challenging dynamics, but ratherthan pull back, we have sought to identify opportunities to expand our platform, attract key personnel, andmove the Bank forward. This confidence stems from our 135-year operating history and deep knowledgeof the communities where we work and clients we serve. Despite uncertain industry conditions, we havecontinued to see the momentum of our long-term strategy building. In 2025, the realization of our hardwork and investments became abundantly evident. For the full year, we earned a record $41.6 million, anearly 50% increase over $27.9 million earned the prior year. We also expanded net income margin 35basis points, to 4.18%, increased our loan portfolio 7.4% to $2 billion, and grew deposits by $157 million, or 7.3%, to $2.3 billion at year end 2025 as compared to year end 2024. While pleased with these results,we are more excited still by the fact that the foundation for them was intentional, solidifying a basefor continued growth, adaptability, and expansion. Core to all this, of course, is our knowledgeable,dedicated staff and the strong relationships they have established with our clients. No matter how sound the base of our business, we know results like those we reported in 2025ultimately derive from methodical planning and execution. For this reason, we continue to invest inour business, adapting and refining our direction to better align with regional and economic develop-ments as well as changing customer needs, always with the goal of positioning ourselves for long-termsuccess. By way of example, we identified early and have frequently referenced our view on theimportance of Wealth Management in deepening existing client relationships and attracting new ones.Our work on this front has proven fruitful: Our dedicated Wealth Management division provides not onlya significant and growing non-correlated income stream to the Bank, but also an important bridge tohelp our busiest, most successful clients manage their personal finances through an outstanding suiteof tools and tailored, professional guidance. Providing effective solutions for a greater share of ourclients’ banking needs helps ensure retention and increases the prospect of additional business, and isjust one part of our strategy to achieve long-term success. Early in 2025, we realigned Hudson Valley Investment Advisors’ (HVIA) trust and our privatebank offerings under the umbrella of Orange Wealth Management. Our goal was to deliver more per-sonalized attention, enhance customer convenience, and better integrate our clients’ business andpersonal banking needs. By fall, this change made it clear that awareness of and access to HVIA’sservices could be further improved, resulting in the rebranding of this group as Orange InvestmentAdvisors (OIA). Our goal here was to implement a more streamlined, client-centric approach to assetmanagement consistent with the overall Orange Bank and Trust brand.In 2025, Orange WealthManagement contributed $14.1 million to the Company’s earnings, a 12.8% increase over the prior yearand a clear demonstration of its financial and strategic value. We expect to see continued growth ofthe division. During the year, we also bolstered the Bank’s more traditional offerings. Building on the successof our initial expansion into the Bronx, we added a second, full-service branch last fall. In an era whenlarger competitors continue to shift from in-person banking to online alternatives, we have found thatbranch locations still offer a distinct advantage, especially when it comes to forging new business re-lationships and gathering low-cost deposits. Another testament to this, is our Yonkers branch success,which opened in 2024, and surpassed 88 million in deposits, at year-end. To remain the pre