1. AND LAUNCHING A NEW NAME.
JUNE 30, 2016 STATEMENT
ORANGE COUNT Y BANCORP, INC.
STRONG
START
WE'RE OFF TO A
THIS IS THE
NEXT LEVEL OF
RELATIONSHIP
BANKING.

3. 3
To Our Stockholders, Customers and Friends:
Orange County Bancorp, Inc. (the “Company”) is pleased to present its unaudited
consolidated financial statements, as of and for the period ended June 30, 2016. This report
includes the financial information of OCBI’s two wholly owned subsidiaries, Orange County Trust
Company (the “Bank”) and Hudson Valley Investment Advisors, Inc. (“HVIA”).
In the Company’s 2015 Annual Report,
we stated our commitment to build on investments
we made during the year. This is bearing fruit, as
results for the first half of 2016 are significantly
improved over our 2015 numbers for the same
period, especially net income, which is up
nearly 300%. This improvement is due primarily to
significant growth in our loan portfolio and core
deposits, which accelerated an increase in net
income, as we intended, with our targeted
investments in people and bricks & mortar.
continued...
PRESIDENT'S MESSAGE
Michael Gilfeather,
President & CEO
2016
(dollars in thousands)
2015
(dollars in thousands)
2016 vs. 2015
Percent Change
Total Assets $899,165 $758,728 19%
Total Loans $495,980 $335,858 48%
Total Securities $307,357 $327,887 -6%
Total Deposits $707,724 $572,510 24%
Net Income $1,479 $(753) 296%
CONSOLIDATED UNAUDITED FINANCIAL RESULTS
Six Months Ended June 30, 2016 and 2015

4. 4
The topic of “low interest rates” has
dominated discussions regarding the business
operations of community banks since the
financial crisis. Despite this, the Bank continues
to source loans and make other investments that
generate a healthy spread over interest expenses
and other ordinary business expenses.
The Bank is dedicated to remaining
independent. The most effective way to do so is
through growth and, in the first half of 2016 and
continuing through to date; the Bank grew on
several fronts. Regulatory approval was obtained
for two new branches in Westchester County;
Mamaroneck and Mount Pleasant. In addition,
we are scouting for a site in Mount Vernon
to establish yet another business-friendly
branch. To support our business banking
culture, the Bank launched a full suite of cash
management/treasury products for businesses,
professionals, entrepreneurs, municipalities and
nonprofit institutions.
The Trust Department, Orange County’s
original business, plays a significant, yet still
growing role in the Bank’s success. Kathryn
Maloney, recruited as the new head of our Trust
Department in 2015, has been hard at work
expanding the Bank’s trust business with an
emphasis on Special Needs Trusts. New business
and fees are up substantially in the group and
Ms. Maloney now has three other trust
professionals working exclusively on this line
of business.
Reflecting our broader geographical
footprint,theBankhasformallychangeditsname
to Orange Bank & Trust Company. This is big
news for a 124-year-old institution, but only the
“second” name change since the Bank opened its
doorsin1892.Thetraditionandheritageofsound
community banking that originated with Orange
County Safe Deposit & Trust Company and
through to Orange County Trust Company will
continue in strong and true measure at Orange
Bank & Trust Company. The name has changed;
the service, people and commitment have not.
ORANGE COUNTY TRUST COMPANY
PRESIDENT'S MESSAGE

5. 5
Gus Scacco joined HVIA as President
& CEO just over a year ago. In that time, Gus
has instilled a highly disciplined investing
approach for the firm’s clients, upgraded trading
systems, and greatly improved financial
reporting and client statement interface
capabilities. Together, these changes have
resulted in greater cost efficiencies, ease of
use and a better overall customer experience.
The firm is also developing a broader range of
investment products for clients, including ones
specifically targeted to the needs of our growing
Trust Department customers. As of June 30,
2016, HVIA managed client assets totaling
$665 million.
Maintaining the ability to deliver value
to our shareholders is my most important job.
The Company’s directors and management
teams of the Bank and HVIA work hard to deliver
on our global commitment to the enterprise.
We are a community organization and
our direct involvement in improving the lives
of our constituents; shareholders, customers/
clients, employees and the community-at-large
is both meaningful and something to which we
consider ourselves duty bound.
Please contact me with any questions
or comments and thank you again for your
confidence and support.
Sincerely,
Michael Gilfeather
President & CEO
HUDSON VALLEY INVESTMENT ADVISORS, INC.
PRESIDENT'S MESSAGE
Hortense Garvin
Business Banker, White Plains Branch

6. 6
CONSOLIDATED STATEMENTS OF CONDITION
June 30, 2016 and 2015 (Unaudited)
(in thousands except for share and per share data) 2016 2015
ASSETS
Cash and due from banks $37,233 $33,226
Investment securities - available-for-sale 307,357 327,887
Restricted investment in bank stocks 4,145 3,818
Loans 495,980 335,858
Allowance for loan losses (6,625) (4,754)
LOANS, NET 489,355 331,104
Premises and equipment 14,351 13,856
Other real estate owned - 1,510
Accrued interest receivable 3,207 2,897
Cash surrender value of bank-owned life insurance 25,369 24,643
Goodwill 5,359 5,359
Intangible assets 3,249 3,534
Other assets 9,540 10,894
TOTAL ASSETS $899,165 $758,728
LIABILITIES AND STOCKHOLDERS' EQUITY
DEPOSITS:
Non-interest bearing $138,174 $103,795
Interest bearing 569,550 468,715
TOTAL DEPOSITS 707,724 572,510
Long-term debt 78,190 73,238
Accrued expenses and other liabilities 16,447 18,870
TOTAL LIABILITIES 802,361 664,618
STOCKHOLDERS' EQUITY
Common stock, $0.50 par value; 5,000,000 and
2,000,000 shares authorized;
1,993,438 and 1,994,875 issued; 1,956,770 and 1,954,956
oustanding at June 30, 2016 and 2015 respectively 997 998
Surplus 70,415 70,593
Undivided profits 27,017 28,171
Accumulated other comprehensive income, net of taxes (121) (3,902)
Treasury stock, at cost; 36,668 and 42,019 shares at June 30,
2016 and 2015, respectively (1,504) (1,750)
TOTAL STOCKHOLDERS’ EQUITY 96,804 94,110
TOTAL LIABILITIES AND STOCKHOLDERS’ EQUITY $899,165 $758,728

7. 7
CONSOLIDATED STATEMENTS OF INCOME
Six Months Ended June 30, 2016 and 2015 (Unaudited)
(in thousands except for share and per share data) 2016 2015
INTEREST INCOME:
Interest and fees on loans $10,715 $8,209
Interest on investment securities:
Taxable 2,523 2,625
Tax exempt 1,199 1,473
Interest on Federal funds sold and other 36 16
TOTAL INTEREST INCOME 14,473 12,323
INTEREST EXPENSE:
Interest on savings and NOW accounts 246 262
Interest on time deposits 407 271
Interest on short-term borrowings - 1
Interest on long-term debt 1,366 1,524
TOTAL INTEREST EXPENSE 2,019 2,058
NET INTEREST INCOME 12,454 10,265
Provision for loan losses 539 2,734
NET INTEREST INCOME AFTER
PROVISION FOR LOAN LOSSES
11,915 7,531
OTHER OPERATING INCOME:
Service charges on deposit accounts 454 535
Trust & investment division income 2,800 2,558
Investment security gains, net 154 640
Earnings on bank-owned life insurance 363 361
Other 354 314
TOTAL OTHER OPERATING INCOME 4,125 4,408
OTHER OPERATING EXPENSES:
Salaries 6,035 5,764
Employee benefits 1,929 1,989
Occupancy expense 1,168 1,109
Furniture and equipment expense 305 243
Professional fees 964 861
Directors’ fees and expenses 377 357
Advertising expenses 365 321
Computer software expense 633 315
FDIC assessment 363 308
Net expenses from foreclosed assets - 571
Other 1,919 1,413
TOTAL OTHER OPERATING EXPENSES 14,058 13,251
Income (loss) before income taxes 1,982 (1,312)
Provison for income taxes 503 (559)
NET INCOME (LOSS) $1,479 $(753)
Basic earnings (loss) per share $0.76 $(0.38)
Weighted average shares outstanding 1,955,581 1,957,455

8. Louis Heimbach, Chairman
David A. Dewilde
Michael Gilfeather
Paul T. McDermott
William D. Morrison
Susan Metzger
Virginia Rizzo
Richard Rowley
Terry R. Saturno
Michael Gilfeather, President & CEO
Michael Gilfeather, President & CEO
Gus Scacco, CEO & Chief Investment Officer
Lou Heimbach, Chairman
Michael Gilfeather
Thomas Guarino
Peter Larkin
Michael Markhoff
Jonathan Rouis
Gus Scacco
O R A N G E B A N K T R U S T . C O M
ORANGE COUNT Y BANCORP, INC.
ORANGE COUNTY BANCORP, INC.
AND ORANGE COUNTY TRUST COMPANY
BOARD OF DIRECTORS
ORANGE COUNTY BANCORP, INC.
ORANGE COUNTY TRUST COMPANY
HUDSON VALLEY INVESTMENT ADVISORS, INC.
HUDSON VALLEY INVESTMENT ADVISORS, INC.
BOARD OF DIRECTORS