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    <div style="text-align: right;"><font style="font-weight: bold;">Registration No. 333-&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font></div>
    <div style="text-align: right;"><font style="font-weight: bold;"></font><font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 180pt" class="TRGRRTFtoHTMLTab"><br>
      </font></div>
    <div style="text-align: center; font-weight: bold;">As filed with the Securities and Exchange Commission on August 4, 2023</div>
    <div style="text-align: center; font-weight: bold;"> <br>
    </div>
    <div style="text-align: center; font-size: 12pt;"><font style="font-weight: bold;">UNITED STATES</font></div>
    <div style="text-align: center; font-size: 12pt;"><font style="font-weight: bold;">SECURITIES AND EXCHANGE COMMISSION<br>
      </font></div>
    <div style="text-align: center; font-size: 12pt;"><font style="font-weight: bold;">Washington, D.C.&#160; 20549</font></div>
    <div style="text-align: center; font-size: 12pt;">_________________________</div>
    <div style="text-align: center; font-size: 12pt;"> <br>
    </div>
    <div style="text-align: center; font-size: 12pt; font-weight: bold;">FORM S-8</div>
    <div style="text-align: center; font-size: 12pt; font-weight: bold;"> <br>
    </div>
    <div style="text-align: center; font-size: 12pt; font-weight: bold;">REGISTRATION STATEMENT</div>
    <div style="text-align: center; font-size: 12pt; font-weight: bold;">UNDER</div>
    <div style="text-align: center; font-size: 12pt; font-weight: bold;">THE SECURITIES ACT OF 1933</div>
    <div style="text-align: center; font-size: 12pt; font-weight: bold;"> <br>
    </div>
    <div style="text-align: center; font-size: 12pt; font-weight: bold;">Orange County Bancorp, Inc.</div>
    <div style="text-align: center; font-size: 8pt;">(Exact Name of Registrant as Specified in its Charter)</div>
    <div><br>
    </div>
    <table cellspacing="0" cellpadding="0" style="font-family: 'Times New Roman', Times, serif; font-size: 10pt; width: 100%; text-align: left; color: #000000;" id="z1beeffc4460b4845afcde22a5912438f">

        <tr>
          <td style="width: 50.02%; vertical-align: top;">
            <div style="text-align: center; font-size: 12pt; font-weight: bold;">Delaware</div>
          </td>
          <td style="width: 49.98%; vertical-align: top;">
            <div style="text-align: center; font-size: 12pt; font-weight: bold;">26-1135778</div>
          </td>
        </tr>
        <tr>
          <td style="width: 50.02%; vertical-align: top;">
            <div style="text-align: center; font-size: 8pt;">(State or Other Jurisdiction of</div>
          </td>
          <td style="width: 49.98%; vertical-align: top;">
            <div style="text-align: center; font-size: 8pt;">(I.R.S. Employer Identification No.)</div>
          </td>
        </tr>
        <tr>
          <td style="width: 50.02%; vertical-align: top;">
            <div style="text-align: center; font-size: 8pt;">Incorporation or Organization)</div>
          </td>
          <td style="width: 49.98%; vertical-align: top;">&#160;</td>
        </tr>

    </table>
    <div><br>
    </div>
    <div style="text-align: center; font-size: 12pt; font-weight: bold;">212 Dolson Avenue</div>
    <div style="text-align: center;"><font style="font-size: 12pt; font-weight: bold;">Middletown, New York 10940</font></div>
    <div style="text-align: center;"><font style="font-size: 12pt; font-weight: bold;"></font><font style="font-size: 8pt;">(Address of Principal Executive Offices)</font><font style="font-size: 12pt; font-weight: bold;"></font></div>
    <div style="text-align: center;"><font style="font-size: 12pt; font-weight: bold;"> <br>
      </font></div>
    <div style="text-align: center;"><font style="font-size: 12pt; font-weight: bold;">Orange County Bancorp, Inc. 2023 Equity Incentive Plan</font></div>
    <div style="text-align: center;"><font style="font-size: 8pt;">(Full Title of the Plan)</font></div>
    <div style="text-align: center;"> <br>
    </div>
    <div style="text-align: center;">Copies to:</div>
    <table cellspacing="0" cellpadding="0" style="font-family: 'Times New Roman', Times, serif; font-size: 10pt; width: 100%; text-align: left; color: #000000;" id="z0e168a235bc547a1a4a7a801ab6cbc56">

        <tr>
          <td style="width: 50.01%; vertical-align: top;">
            <div style="text-align: center;">Michael J. Gilfeather</div>
          </td>
          <td style="width: 49.99%; vertical-align: top;">
            <div style="text-align: center;">Benjamin M. Azoff, Esq.</div>
          </td>
        </tr>
        <tr>
          <td style="width: 50.01%; vertical-align: top;">
            <div style="text-align: center;">President and Chief Executive Officer</div>
          </td>
          <td style="width: 49.99%; vertical-align: top;">
            <div style="text-align: center;">Brendan M. Saxon, Esq.</div>
          </td>
        </tr>
        <tr>
          <td style="width: 50.01%; vertical-align: top;">
            <div style="text-align: center;">Orange County Bancorp, Inc.</div>
          </td>
          <td style="width: 49.99%; vertical-align: top;">
            <div style="text-align: center;">Luse Gorman, PC</div>
          </td>
        </tr>
        <tr>
          <td style="width: 50.01%; vertical-align: top;">
            <div style="text-align: center;">212 Dolson Avenue</div>
          </td>
          <td style="width: 49.99%; vertical-align: top;">
            <div style="text-align: center;">5335 Wisconsin Ave., N.W., Suite 780</div>
          </td>
        </tr>
        <tr>
          <td style="width: 50.01%; vertical-align: top;">
            <div style="text-align: center;">Middletown, New York 10940</div>
          </td>
          <td style="width: 49.99%; vertical-align: top;">
            <div style="text-align: center;">Washington, DC 20015-2035</div>
          </td>
        </tr>
        <tr>
          <td style="width: 50.01%; vertical-align: top;">
            <div style="text-align: center;">(845) 341-5000</div>
          </td>
          <td style="width: 49.99%; vertical-align: top;">
            <div style="text-align: center;">(202) 274-2000</div>
          </td>
        </tr>
        <tr>
          <td style="width: 50.01%; vertical-align: top;">
            <div style="text-align: center;">(Name, Address and Telephone</div>
          </td>
          <td style="width: 49.99%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 50.01%; vertical-align: top;">
            <div style="text-align: center;">Number of Agent for Service)</div>
          </td>
          <td style="width: 49.99%; vertical-align: top;">&#160;</td>
        </tr>

    </table>
    <div><br>
    </div>
    <div style="text-align: justify;">Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, smaller reporting company, or an emerging growth company. See the definitions of &#8220;large
      accelerated filer,&#8221; &#8220;accelerated filer,&#8221; &#8220;smaller reporting company&#8221; and &#8220;emerging growth company&#8221; in Rule 12b-2 of the Securities Exchange Act of 1934, as amended:</div>
    <div><br>
    </div>
    <table cellspacing="0" cellpadding="0" style="font-family: 'Times New Roman', Times, serif; font-size: 10pt; width: 100%; text-align: left; color: #000000;" id="z4f63c2bdc6bf47f9b495e12d5000c1a2">

        <tr>
          <td style="width: 66.66%; vertical-align: top;">
            <div>Large accelerated filer &#9744;</div>
          </td>
          <td style="width: 33.34%; vertical-align: top;">
            <div>Accelerated filer &#9744;</div>
          </td>
        </tr>
        <tr>
          <td style="width: 66.66%; vertical-align: top;">
            <div>Non-accelerated filer&#160; &#8999;</div>
          </td>
          <td style="width: 33.34%; vertical-align: top;">
            <div>Smaller reporting company&#8999;</div>
          </td>
        </tr>
        <tr>
          <td style="width: 66.66%; vertical-align: top;">
            <div>Emerging growth company &#8999;</div>
          </td>
          <td style="width: 33.34%; vertical-align: top;">&#160;</td>
        </tr>

    </table>
    <div><br>
    </div>
    <div style="text-align: justify;">If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to
      Section 7(a)(2)(B) of the Securities Act. &#9744;</div>
    <div><br>
    </div>
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    <div style="text-align: justify; margin-bottom: 12pt;"><font style="font-weight: bold;">PART I.</font><font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 72pt" class="TRGRRTFtoHTMLTab">&#160;</font><font style="font-weight: bold;">INFORMATION


        REQUIRED IN THE SECTION 10(a) PROSPECTUS</font></div>
    <div style="text-align: justify; margin-bottom: 12pt;"><font style="font-weight: bold;">Items 1 and 2.</font><font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 108pt" class="TRGRRTFtoHTMLTab">&#160;</font><font style="font-weight: bold;">Plan Information; and Registrant Information and Employee Plan Annual Information</font></div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">The documents containing the information specified in Part I of Form S-8 have been or will be sent or given to participants in the Orange County Bancorp, Inc. 2023 Equity
      Incentive Plan (the &#8220;Plan&#8221;) as specified by Rule 428(b)(1) promulgated by the Securities and Exchange Commission (the &#8220;Commission&#8221;) under the Securities Act of 1933, as amended (the &#8220;Securities Act&#8221;).</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Such documents are not being filed with the Commission but constitute (along with the documents incorporated by reference into this Registration Statement pursuant to Item 3 of
      Part II hereof) a prospectus that meets the requirements of Section 10(a) of the Securities Act.</div>
    <div style="text-align: justify; margin-bottom: 12pt;"><font style="font-weight: bold;">PART II.</font><font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 72pt" class="TRGRRTFtoHTMLTab">&#160;</font><font style="font-weight: bold;">INFORMATION


        REQUIRED IN THE REGISTRATION STATEMENT</font></div>
    <div style="text-align: justify; margin-bottom: 12pt;"><font style="font-weight: bold;">Item 3.</font><font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 72pt" class="TRGRRTFtoHTMLTab">&#160;</font><font style="font-weight: bold;">Incorporation


        of Documents by Reference</font></div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">The following documents previously filed by Orange County Bancorp, Inc. (the &#8220;Company&#8221;) with the Commission under the Securities Exchange Act of 1934, as amended (the &#8220;Exchange
      Act&#8221;), are incorporated herein by reference (other than any such documents or portions thereof that are furnished under Item 2.02 or Item 7.01 of Form&#160;8-K,&#160;unless otherwise indicated therein, including any exhibits included with such items):</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">(a)<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>The Company&#8217;s Annual Report on Form 10-K for the year ended
      December 31, 2022, filed with the Commission on <a href="https://www.sec.gov/ix?doc=/Archives/edgar/data/0001754226/000155837023004543/tmb-20221231x10k.htm">March 24, 2023</a> (File No. 001-40711) pursuant to Section 13(a) of the Exchange Act
      (including information specifically incorporated by reference therein from the Company&#8217;s definitive proxy statement on Schedule 14A, filed on <a href="https://www.sec.gov/Archives/edgar/data/1754226/000110465923045321/tm232120-1_def14a.htm">April
        14, 2023</a>);</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">(b)<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>The Company&#8217;s Quarterly Report on Form 10-Q for the quarter
      ended March 31, 2023, filed with the Commission on <a href="https://www.sec.gov/ix?doc=/Archives/edgar/data/1754226/000155837023009958/tmb-20230331x10q.htm">May 15, 2023</a> (File No. 001-40711);</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">(c)<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>The Company&#8217;s Current Reports on Form 8-K filed with the
      Commission on <a href="https://www.sec.gov/ix?doc=/Archives/edgar/data/0001754226/000110465923023324/tm237288d1_8k.htm">February 17, 2023</a>, <a href="https://www.sec.gov/ix?doc=/Archives/edgar/data/1754226/000110465923062675/tm2316319d1_8k.htm">May


        19, 2023</a>, <a href="https://www.sec.gov/ix?doc=/Archives/edgar/data/1754226/000110465923064182/tm2316886d1_8k.htm">May 24, 2023</a>, and <a href="https://www.sec.gov/ix?doc=/Archives/edgar/data/1754226/000094337423000271/form8k_062623.htm">June


        26, 2023</a> (File No. 001-40711 for all); and</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">(d)<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>The description of the Company&#8217;s common stock contained in
      the Registration Statement on Form 8-A, filed with the Commission on <a href="https://www.sec.gov/Archives/edgar/data/1754226/000094337421000383/form8a_080421.htm">August 4, 2021</a>,<font style="font-weight: bold;">&#160;</font>to register the Company's
      common stock under the Exchange Act (File No. 000-40711), including any subsequent amendments or reports filed for the purpose of updating such description.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">All documents subsequently filed by the Company with the Commission pursuant to Sections 13(a), 13(c), 14, or 15(d) of the Exchange Act, after the date hereof, and prior to the
      filing of a post-effective amendment which indicates that all securities offered hereby have been sold or which deregisters all securities then remaining unsold, shall be deemed incorporated by reference into this Registration Statement and to be a
      part thereof from the date of the filing of such documents.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Any statement contained in the documents incorporated, or deemed to be incorporated, by reference herein or therein shall be deemed to be modified or superseded for purposes of
      this Registration Statement and the prospectus to the extent that a statement contained herein or therein or in any other subsequently filed document which also is, or is deemed to be, incorporated by reference herein or therein modifies or
      supersedes such statement.&#160; Any such statement so modified or superseded shall not be deemed, except as so modified or superseded, to constitute a part of this Registration Statement and the prospectus.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">All information appearing in this Registration Statement and the prospectus is qualified in its entirety by the detailed information, including financial statements, appearing in
      the documents incorporated herein or therein by reference.</div>
    <div style="text-align: justify; margin-bottom: 12pt; font-weight: bold;">Item 4.&#160; Description of Securities</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Not applicable.</div>
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    <div style="text-align: justify; margin-bottom: 12pt; font-weight: bold;">Item 5.&#160; Interests of Named Experts and Counsel</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">None.</div>
    <div style="text-align: justify; margin-bottom: 12pt; font-weight: bold;">Item 6.&#160;&#160;Indemnification of Directors and Officers</div>
    <div>
      <div style="text-align: justify; text-indent: 36pt;">Article X of the Certificate of Incorporation and Article VI of the Bylaws of Orange County Bancorp, Inc. (the &#8220;Corporation&#8221;) set forth circumstances under which directors, officers, employees and
        agents of the Corporation may be insured or indemnified against liability which they incur in their capacities as such:</div>
      <div><br>
      </div>
    </div>
    <div style="text-indent: 36pt; font-weight: bold;">ARTICLE&#160;X.&#160; Limitation on Liability.</div>
    <div><br>
    </div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">A director of the Corporation shall not be personally liable to the Corporation or its stockholders for monetary damages for breach of fiduciary duty as a director, except for
      liability: (i) for any breach of the director's duty of loyalty to the Corporation or its stockholders; (ii) for acts or omissions not in good faith or which involve intentional misconduct or a knowing violation of law; (iii) under Section 174 of the
      Delaware General Corporation Law; or (iv) for any transaction from which the director derived an improper personal benefit. If the Delaware General Corporation Law is amended to authorize corporate action further eliminating or limiting the personal
      liability of directors, then the liability of a director of the Corporation shall be eliminated or limited to the fullest extent permitted by the Delaware General Corporation Law, as so amended.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Any repeal or modification of the foregoing paragraph by the stockholders of the Corporation shall not adversely affect any right or protection of a director of the Corporation
      existing at the time of such repeal or modification.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt; font-weight: bold;">ARTICLE VI. Indemnification</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 1. Actions, Suits or Proceedings Other Than Those by or in the Right of the Corporation. Subject to Section 3 of this Article VI, the Corporation shall indemnify any
      person who was or is a party or is threatened to be made a party to any threatened, pending or completed action, suit or proceeding, whether civil, criminal, administrative or investigative (other than an action by or in the right of the Corporation)
      by reason of the fact that the person is or was or has agreed to become a director or officer of the Corporation, or is or was a director or officer of the Corporation serving at the request of the Corporation as a director, officer, employee or
      agent of another corporation, partnership, joint venture, trust, employee benefit plan or other enterprise, against expenses (including attorney's fees), judgments, fines and amounts paid in settlement actually and reasonably incurred by the person
      in connection with such action, suit or proceeding if the person acted in good faith and in a manner the person reasonably believed to be in or not opposed to the best interests of the Corporation, and, with respect to any criminal action or
      proceeding, had no reasonable cause to believe the person's conduct was unlawful. The termination of any action, suit or proceeding by judgment, order, settlement, conviction, or upon a plea of nolo contendere or its equivalent, shall not, of itself,
      create a presumption that the person did not act in good faith and in a manner which the person reasonably believed to be in or not opposed to the best interests of the corporation, and, with respect to criminal action or proceeding, had reasonable
      cause to believe that the person's conduct was unlawful.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 2. Actions, Suits or Proceedings by or in the Right of the Corporation. Subject to Section 3 of this Article VI, the Corporation shall indemnify any person who was or is
      a party or is threatened to be made a party to any threatened, pending or completed action or suit by or in the right of the Corporation to procure a judgment in its favor by reason of the fact that he is or was a director or officer of the
      Corporation, or is or was a director or officer of the Corporation serving at the request of the Corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust, employee benefit plan or other
      enterprise against expenses (including attorneys' fees) actually and reasonably incurred by him in connection with the defense or settlement of such action or suit if he acted in good faith and in a manner he reasonably believed to be in or not
      opposed to the best interests of the Corporation; except that no indemnification shall be made in respect of any claim, issue or matter as to which such person shall have been adjudged to be liable to the Corporation unless and only to the extent
      that the Court of Chancery or the court in which such action or suit was brought shall determine upon application that, despite the adjudication of liability but in view of all the circumstances of the case, such person is fairly and reasonably
      entitled to indemnity for such expenses which the Court of Chancery or such other court shall deem proper.</div>
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    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 3. Authorization of Indemnification. Any indemnification under this Article VI (unless ordered by a court) shall be made by the Corporation only as authorized in the
      specific case upon a determination that indemnification of the present or former director or officer is proper in the circumstances because he or she has met the applicable standard of conduct set forth in Section 1 or Section 2 of this Article VI,
      as the case may be. Such determination shall be made (i) by the Board by a majority vote of directors who were not parties to such action, suit or proceeding, even though less than a quorum, (ii) by a committee of such directors designated by
      majority vote of such directors, even though less than a quorum; (iii) if there are no such directors, or if such directors so direct, by independent legal counsel in a written opinion, or (iv) by the stockholders. To the extent, however, that a
      director or officer of the Corporation has been successful on the merits or otherwise in defense of any action, suit or proceeding described above, or in defense of any claim, issue or matter therein, he or she shall be indemnified against expenses
      (including attorneys' fees) actually and reasonably incurred by him or her in connection therewith, without the necessity of authorization in the specific case.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 4. Indemnification by a Court. Notwithstanding any contrary determination in the specific case under Section 3 of this Article VI, and notwithstanding the absence of any
      determination thereunder, any director or officer may apply to any court of competent jurisdiction in the State of Delaware for indemnification to the extent otherwise permissible under Sections 1 and 2 of this Article VI. The basis of such
      indemnification by a court shall be a determination by such court that indemnification of the director or officer is proper in the circumstances because he or she has met the applicable standards of conduct set forth in Sections 1 or 2 of this
      Article VI, as the case may be. Neither a contrary determination in the specific case under Section 3 of this Article VI nor the absence of any determination thereunder shall be a defense to such application or create a presumption that the director
      or officer seeking indemnification has not met any applicable standard of conduct. Notice of any application for indemnification pursuant to this Section 4 shall be given to the Corporation promptly upon the filing of such application. If successful,
      in whole or in part, the director or officer seeking indemnification shall also be entitled to be paid the expense of prosecuting such application.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 5. Expenses Payable in Advance. Expenses incurred by a director or officer in defending or investigating a threatened or pending action, suit or proceeding shall be paid
      by the Corporation in advance of the final disposition of such action, suit or proceeding upon receipt of an undertaking by or on behalf of such director or officer to repay such amount if it shall ultimately be determined that he or she is not
      entitled to be indemnified by the Corporation as authorized in this Article VI.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 6. Nonexclusivity of Indemnification and Advancement of Expenses. The indemnification and advancement of expenses provided by or granted pursuant to this Article VI shall
      not be deemed exclusive of any other rights to which those seeking indemnification or advancement of expenses may be entitled under any Bylaws, agreement, contract, vote of stockholders or disinterested directors or pursuant to the direction (however
      embodied) of any court of competent jurisdiction or otherwise, both as to action in his or her official capacity and as to action in another capacity while holding such office, it being the policy of the Corporation that indemnification of the
      persons specified in Sections I and 2 of this Article VI shall be made to the fullest extent permitted by law. The provisions of this Article VI shall not be deemed to preclude the indemnification of any person who is not specified in Sections I or 2
      of this Article VI but whom the Corporation has the power or obligation to indemnify under the provisions of the Delaware General Corporation Law or otherwise.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 7. Insurance. The Corporation may purchase and maintain insurance on behalf of any person who is or was a director or officer of the Corporation, or is or was a director
      or officer of the Corporation serving at the request of the Corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust, employee benefit plan or other enterprise against any liability asserted
      against him or her and incurred by him or her in any such capacity, or arising out of his or her status as such, whether or not the Corporation would have the power or the obligation to indemnify him or her against such liability under the provisions
      of this Article VI.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 8. Certain Definitions. For purposes of this Article VI, references to "the Corporation" shall include, in addition to the resulting corporation, any constituent
      corporation (including any constituent of a constituent) absorbed in a consolidation or merger which, if its separate existence had continued, would have had power and authority to indemnify its directors or officers, so that any person who is or was
      a director or officer of such constituent corporation, or is or was a director or officer of such constituent corporation serving at the request of such constituent corporation as a director, officer, employee or agent of another corporation,
      partnership, joint venture, trust, employee benefit plan or other enterprise, shall stand in the same position under the provisions of this Article VI with respect to the resulting or surviving corporation as he or she would have with respect to such
      constituent corporation if its</div>
    <div style="clear: both; margin-top: 10pt; margin-bottom: 10pt;" class="BRPFPageBreakArea">
      <div style="text-align: center;" class="BRPFPageNumberArea"><font style="font-size: 8pt; font-weight: normal; font-style: normal;" class="BRPFPageNumber">3</font></div>
      <div style="page-break-after: always;" class="BRPFPageBreak">
        <hr noshade="noshade" style="margin: 4px 0px; width: 100%; border-width: 0; height: 2px; color: #000000; background-color: #000000; clear: both;"></div>
    </div>
    <div style="text-align: justify; margin-bottom: 12pt;">separate existence had continued. For purposes of this Article VI, references to "fines" shall include any excise taxes assessed on a person with respect to an employee benefit plan; and references
      to "serving at the request of the Corporation" shall include any service as a director, officer, employee or agent of the Corporation which imposes duties on, or involves services by, such director or officer with respect to an employee benefit plan,
      its participants or beneficiaries; and a person who acted in good faith and in a manner he reasonably believed to be in the interest of the participants and beneficiaries of an employee benefit plan shall be deemed to have acted in a manner "not
      opposed to the best interests of the Corporation" as referred to in this Article VI.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 9. Survival of Indemnification and Advancement of Expenses. The indemnification and advancement of expenses provided by, or granted pursuant to, this Article VI shall,
      unless otherwise provided when authorized or ratified, continue as to a person who has ceased to be a director or officer and shall inure to the benefit of the heirs, executors and administrators of such a person.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 10. Limitation on Indemnification. Notwithstanding anything contained in this Article VI to the contrary, except for proceedings to enforce rights to indemnification
      (which shall be governed by Section 4 hereof), the Corporation shall not be obligated to indemnify any director or officer in connection with a proceeding (or part thereof) initiated by such person unless such proceeding (or part thereof) was
      authorized or consented to by the Board of the Corporation.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Section 11. Indemnification of Employees and Agents. The Corporation may, to the extent authorized from time to time by the Board, provide rights to indemnification and to the
      advancement of expenses to employees and agents of the Corporation similar to those conferred in this Article VI to directors and officers of the Corporation.</div>
    <div style="text-align: justify; font-weight: bold;">Item 7.&#160; Exemption From Registration Claimed.</div>
    <div><br>
    </div>
    <div style="text-align: justify; text-indent: 36pt;">Not applicable.</div>
    <div><br>
    </div>
    <div style="text-align: justify; font-weight: bold;">Item 8.&#160; List of Exhibits.</div>
    <div><br>
    </div>
    <table cellspacing="0" cellpadding="0" style="font-family: 'Times New Roman', Times, serif; font-size: 10pt; width: 100%; text-align: left; color: #000000;" id="zda1ada6e632b4477a24e7cd8ef7dc5a3">

        <tr>
          <td style="width: 19.91%; vertical-align: bottom; border-bottom: #000000 2px solid;">
            <div style="text-align: center;">Regulation S-K</div>
            <div style="text-align: center;">Exhibit Number</div>
          </td>
          <td style="width: 2.82%; vertical-align: bottom;">&#160;</td>
          <td style="width: 77.26%; vertical-align: bottom; border-bottom: #000000 2px solid;">
            <div style="text-align: center;">Document</div>
          </td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">&#160;</td>
          <td style="width: 2.82%; vertical-align: top;">&#160;</td>
          <td style="width: 77.26%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">
            <div style="text-align: center;"><a href="https://www.sec.gov/Archives/edgar/data/1754226/000110465921090389/tm2116829d4_ex4-1.htm">4</a></div>
          </td>
          <td style="width: 2.82%; vertical-align: top;"><br>
          </td>
          <td style="width: 77.26%; vertical-align: top;">
            <div style="text-align: justify;"><a href="https://www.sec.gov/Archives/edgar/data/1754226/000110465921090389/tm2116829d4_ex4-1.htm">Form of Common Stock Certificate (incorporated by reference to Exhibit 4.1 to the Registration Statement on
                Form S-1 (File No. 333-257781), as amended, filed by the Company under the Securities Act with the Commission on July 9, 2021)</a></div>
          </td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">&#160;</td>
          <td style="width: 2.82%; vertical-align: top;">&#160;</td>
          <td style="width: 77.26%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">
            <div style="text-align: center;"><a href="ex5-s8_080423.htm">5</a></div>
          </td>
          <td style="width: 2.82%; vertical-align: top;"><br>
          </td>
          <td style="width: 77.26%; vertical-align: top;">
            <div><a href="ex5-s8_080423.htm">Opinion of Luse Gorman, PC</a></div>
          </td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">&#160;</td>
          <td style="width: 2.82%; vertical-align: top;">&#160;</td>
          <td style="width: 77.26%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">
            <div style="text-align: center;"><a href="https://www.sec.gov/Archives/edgar/data/1754226/000110465923045321/tm232120-1_def14a.htm">10.1</a></div>
          </td>
          <td style="width: 2.82%; vertical-align: top;"><br>
          </td>
          <td style="width: 77.26%; vertical-align: top;">
            <div style="text-align: justify;"><a href="https://www.sec.gov/Archives/edgar/data/1754226/000110465923045321/tm232120-1_def14a.htm">Orange County Bancorp, Inc. 2023 Equity Incentive Plan (incorporated by reference to Appendix A to the proxy
                statement for the Annual Meeting of Shareholders of Orange County Bancorp, Inc., filed under the Exchange Act on April 14, 2023 (File No. 001-40711))</a></div>
          </td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">&#160;</td>
          <td style="width: 2.82%; vertical-align: top;">&#160;</td>
          <td style="width: 77.26%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">
            <div style="text-align: center;"><a href="ex10-2s8_080423.htm">10.2</a></div>
          </td>
          <td style="width: 2.82%; vertical-align: top;"><br>
          </td>
          <td style="width: 77.26%; vertical-align: top;">
            <div><a href="ex10-2s8_080423.htm">Form of Restricted Stock Unit Agreement (Non-Employee Directors)</a></div>
          </td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">&#160;</td>
          <td style="width: 2.82%; vertical-align: top;">&#160;</td>
          <td style="width: 77.26%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">
            <div style="text-align: center;"><a href="ex10-3s8_080423.htm">10.3</a></div>
          </td>
          <td style="width: 2.82%; vertical-align: top;"><br>
          </td>
          <td style="width: 77.26%; vertical-align: top;">
            <div><a href="ex10-3s8_080423.htm">Form of Restricted Stock Unit Agreement (Employee/Consultants)</a></div>
          </td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">&#160;</td>
          <td style="width: 2.82%; vertical-align: top;">&#160;</td>
          <td style="width: 77.26%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">
            <div style="text-align: center;"><a href="ex10-4s8_080423.htm">10.4</a></div>
          </td>
          <td style="width: 2.82%; vertical-align: top;"><br>
          </td>
          <td style="width: 77.26%; vertical-align: top;">
            <div><a href="ex10-4s8_080423.htm">Form of Performance Restricted Stock Unit Agreement (Employee)</a></div>
          </td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">&#160;</td>
          <td style="width: 2.82%; vertical-align: top;">&#160;</td>
          <td style="width: 77.26%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">
            <div style="text-align: center;"><a href="ex5-s8_080423.htm">23.1</a></div>
          </td>
          <td style="width: 2.82%; vertical-align: top;"><br>
          </td>
          <td style="width: 77.26%; vertical-align: top;">
            <div><a href="ex5-s8_080423.htm">Consent of Luse Gorman, PC (contained in Exhibit 5)</a></div>
          </td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">&#160;</td>
          <td style="width: 2.82%; vertical-align: top;">&#160;</td>
          <td style="width: 77.26%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">
            <div style="text-align: center;"><a href="ex23-2s8_080423.htm">23.2</a></div>
          </td>
          <td style="width: 2.82%; vertical-align: top;"><br>
          </td>
          <td style="width: 77.26%; vertical-align: top;">
            <div><a href="ex23-2s8_080423.htm">Consent of Crowe LLP (Independent Registered Public Accounting Firm)</a></div>
          </td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">&#160;</td>
          <td style="width: 2.82%; vertical-align: top;">&#160;</td>
          <td style="width: 77.26%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">
            <div style="text-align: center;"><a href="#POWEROFATTORNEY">24</a></div>
          </td>
          <td style="width: 2.82%; vertical-align: top;"><br>
          </td>
          <td style="width: 77.26%; vertical-align: top;">
            <div><a href="#POWEROFATTORNEY">Power of Attorney (contained on signature page)</a></div>
          </td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">&#160;</td>
          <td style="width: 2.82%; vertical-align: top;">&#160;</td>
          <td style="width: 77.26%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 19.91%; vertical-align: top;">
            <div style="text-align: center;"><a href="ex107-s8_080423.htm">107</a></div>
          </td>
          <td style="width: 2.82%; vertical-align: top;"><br>
          </td>
          <td style="width: 77.26%; vertical-align: top;">
            <div><a href="ex107-s8_080423.htm">Filing Fee Table</a></div>
          </td>
        </tr>

    </table>
    <div><br>
    </div>
    <div style="clear: both; margin-top: 10pt; margin-bottom: 10pt;" class="BRPFPageBreakArea">
      <div style="text-align: center;" class="BRPFPageNumberArea"><font style="font-size: 8pt; font-weight: normal; font-style: normal;" class="BRPFPageNumber">4</font></div>
      <div style="page-break-after: always;" class="BRPFPageBreak">
        <hr noshade="noshade" style="margin: 4px 0px; width: 100%; border-width: 0; height: 2px; color: #000000; background-color: #000000; clear: both;"></div>
    </div>
    <div><br>
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        <tr>
          <td style="width: 72pt; vertical-align: top; font-weight: bold;">Item 9.</td>
          <td style="width: auto; vertical-align: top; text-align: justify;">
            <div style="font-weight: bold;">Undertakings</div>
          </td>
        </tr>

    </table>
    <div><br>
    </div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">The undersigned registrant hereby undertakes:</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">1.<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>To file, during any period in which offers or sales are
      being made, a post-effective amendment to the Registration Statement:</div>
    <div style="text-align: justify; text-indent: 72pt; margin-bottom: 12pt;">(i)<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>to include any prospectus required by Section 10(a)(3) of
      the Securities Act;</div>
    <div style="text-align: justify; text-indent: 72pt; margin-bottom: 12pt;">(ii)<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>to reflect in the prospectus any facts or events arising
      after the effective date of the registration statement (or the most recent post-effective amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set forth in the registration statement.&#160;
      Notwithstanding the foregoing, any increase or decrease in volume of securities offered (if the total dollar value of securities offered would not exceed that which was registered) and any deviation from the low or high end of the estimated maximum
      offering range may be reflected in the form of prospectus filed with the Commission pursuant to Rule 424(b) (section 230.424(b)) if, in the aggregate, the changes in volume and price represent no more than 20% change in the maximum aggregate offering
      price set forth in the &#8220;Calculation of Registration Fees&#8221; table in the effective registration statement;</div>
    <div style="text-align: justify; text-indent: 72pt; margin-bottom: 12pt;">(iii)<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>to include any material information with respect to the
      plan of distribution not previously disclosed in this Registration Statement or any material change to such information in this Registration Statement;</div>
    <div style="text-align: justify; margin-bottom: 12pt;">provided, however, that paragraphs 1(i) and 1(ii) above do not apply if the information required to be included in a post-effective amendment by these paragraphs is contained in reports filed with
      or furnished to the Commission by the Company pursuant to Section 13 or Section 15(d) of the Exchange Act that are incorporated by reference in this Registration Statement.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">2.<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>That, for the purpose of determining any liability under the
      Securities Act, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial <font style="font-style: italic;">bona fide</font> offering thereof;</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">3.<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>To remove from registration by means of a post-effective
      amendment any of the securities being registered which remain unsold at the termination of the offering;</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">4.<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>That, for purposes of determining any liability under the
      Securities Act, each filing of the registrant's annual report pursuant to Section 13(a) or 15(d) of the Exchange Act (and, where applicable, each filing of an employee benefit plan's annual report pursuant to Section 15(d) of the Exchange Act) that
      is incorporated by reference in the registration statement shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide
      offering thereof; and</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">5.<font style="display: inline-block; text-indent: 0px; font-size: 1px; width: 36pt" class="TRGRRTFtoHTMLTab">&#160;</font>Insofar as indemnification for liabilities arising under the
      Securities Act may be permitted to directors, officers and controlling persons of the registrant pursuant to the foregoing provisions, or otherwise, the registrant has been advised that in the opinion of the Commission such indemnification is against
      public policy as expressed in the Securities Act and is, therefore, unenforceable.&#160; In the event that a claim for indemnification against such liabilities (other than the payment by the registrant of expenses incurred or paid by a director, officer
      or controlling person of the registrant in the successful defense of any action, suit or proceeding) is asserted by such director, officer or controlling person in connection with the securities being registered, the registrant will, unless in the
      opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question whether such indemnification by it is against public policy as expressed in the Securities Act and will be
      governed by the final adjudication of such issue.</div>
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    <div style="text-align: center; font-weight: bold;">SIGNATURES</div>
    <div><br>
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    <div style="text-align: justify; text-indent: 36pt;"><font style="font-weight: bold;">The Registrant.</font>&#160; Pursuant to the requirements of the Securities Act of 1933, as amended, the Registrant certifies that it has reasonable grounds to believe
      that it meets all of the requirements for filing on Form S-8 and has duly caused this Registration Statement on Form S-8 to be signed on its behalf by the undersigned, thereunto duly authorized, in the City of Middletown, State of New York, on August
      4, 2023.</div>
    <div style="margin-bottom: 12pt;"><br>
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        <tr>
          <td style="width: 41.91%; vertical-align: top;">&#160;</td>
          <td style="width: 9.93%; vertical-align: top;">&#160;</td>
          <td style="width: 48.16%; vertical-align: top;">
            <div style="text-align: justify; font-weight: bold;">ORANGE COUNTY BANCORP, INC.</div>
          </td>
        </tr>
        <tr>
          <td style="width: 41.91%; vertical-align: top;">&#160;</td>
          <td style="width: 9.93%; vertical-align: top;">&#160;</td>
          <td style="width: 48.16%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 41.91%; vertical-align: top;">&#160;</td>
          <td style="width: 9.93%; vertical-align: top;">&#160;</td>
          <td style="width: 48.16%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 41.91%; vertical-align: top;">&#160;</td>
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            <div style="text-align: right;">By:&#160;&#160; <br>
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          <td style="width: 48.16%; vertical-align: top; border-bottom: #000000 2px solid;">&#160;/s/ Michael J. Gilfeather<br>
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        <tr>
          <td style="width: 41.91%; vertical-align: top;">&#160;</td>
          <td style="width: 9.93%; vertical-align: top;">&#160;</td>
          <td style="width: 48.16%; vertical-align: top;">
            <div style="text-align: justify;">Michael J. Gilfeather</div>
          </td>
        </tr>
        <tr>
          <td style="width: 41.91%; vertical-align: top;">&#160;</td>
          <td style="width: 9.93%; vertical-align: top;">&#160;</td>
          <td style="width: 48.16%; vertical-align: top;">
            <div style="text-align: justify;">President and Chief Executive Officer</div>
          </td>
        </tr>
        <tr>
          <td style="width: 41.91%; vertical-align: top;">&#160;</td>
          <td style="width: 9.93%; vertical-align: top;">&#160;</td>
          <td style="width: 48.16%; vertical-align: top;">
            <div style="text-align: justify;">(Duly Authorized Representative)</div>
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    </table>
    <div><br>
    </div>
    <div><br>
    </div>
    <div><br>
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    <div style="text-align: center; font-weight: bold;"><a name="POWEROFATTORNEY"><!--Anchor--></a>POWER OF ATTORNEY</div>
    <div><br>
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    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">We, the undersigned directors and officers of Orange County Bancorp, Inc. (the &#8220;Company&#8221;) hereby severally constitute and appoint Michael J. Gilfeather, as our true and lawful
      attorney and agent, to do any and all things in our names in the capacities indicated below which said Michael J. Gilfeather may deem necessary or advisable to enable the Company to comply with the Securities Act of 1933, as amended, and any rules,
      regulations and requirements of the Securities and Exchange Commission, in connection with the registration of shares of Company common stock to be granted and shares of Company common stock to be issued upon the exercise of stock options to be
      granted under the Orange County Bancorp, Inc. 2023 Equity Incentive Plan, including specifically, but not limited to, power and authority to sign for us in our names in the capacities indicated below the registration statement and any and all
      amendments (including post-effective amendments) thereto; and we hereby approve, ratify and confirm all that said Michael J. Gilfeather shall do or cause to be done by virtue thereof.</div>
    <div style="text-align: justify; text-indent: 36pt; margin-bottom: 12pt;">Pursuant to the requirements of the Securities Act, this registration statement has been signed by the following persons in the capacities and on the date indicated.</div>
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        <tr>
          <td style="width: 29.13%; vertical-align: top; border-bottom: 2px solid black;">
            <div>Signatures</div>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
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          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
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          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
        </tr>
        <tr>
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          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
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          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
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        <tr>
          <td style="width: 29.13%; vertical-align: top;">
            <div>Michael J. Gilfeather</div>
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          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
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          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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        <tr>
          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">
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          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">&#160;</td>
          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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        <tr>
          <td style="width: 29.13%; vertical-align: top; border-bottom: #000000 2px solid;">&#160;/s/ Michael Lesler<br>
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          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">
            <div>Senior Vice President and Chief</div>
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          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
          </td>
        </tr>
        <tr>
          <td style="width: 29.13%; vertical-align: top;">
            <div>Michael Lesler</div>
          </td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">
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          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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        <tr>
          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">
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          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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        <tr>
          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">&#160;</td>
          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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        <tr>
          <td style="width: 29.13%; vertical-align: top; border-bottom: #000000 2px solid;">&#160;/s/ Jonathan F. Rouis<br>
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          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">
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          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
          </td>
        </tr>
        <tr>
          <td style="width: 29.13%; vertical-align: top;">
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          </td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">&#160;</td>
          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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        <tr>
          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">&#160;</td>
          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">&#160;</td>
          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top; border-bottom: #000000 2px solid;">&#160;/s/ Louis Heimbach<br>
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          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">
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          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
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        <tr>
          <td style="width: 29.13%; vertical-align: top;">
            <div>Louis Heimbach</div>
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          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">&#160;</td>
          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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        <tr>
          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">&#160;</td>
          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 3.94%; vertical-align: top;">&#160;</td>
          <td colspan="3" style="width: 33.84%; vertical-align: top;">&#160;</td>
          <td style="width: 3.96%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td colspan="2" style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
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          <td colspan="2" style="width: 4.52%; vertical-align: top;">&#160;</td>
          <td style="width: 31.76%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 30.8%; vertical-align: top;">
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          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
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          <td style="width: 29.13%; vertical-align: top;">
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          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top; border-bottom: #000000 2px solid;">&#160;/s/ Marianna R. Kennedy<br>
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          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">
            <div>Director</div>
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          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
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          <td style="width: 29.13%; vertical-align: top;">
            <div>Marianna R. Kennedy</div>
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          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 30.8%; vertical-align: top;">
            <div>Director</div>
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          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
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          <td style="width: 29.13%; vertical-align: top;">
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          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top; border-bottom: #000000 2px solid;">&#160;/s/ Richard B. Rowley<br>
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          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">
            <div>Director</div>
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          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
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          <td style="width: 29.13%; vertical-align: top;">
            <div>Richard B. Rowley</div>
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          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top; border-bottom: #000000 2px solid;">&#160;/s/ Terry R. Saturno<br>
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          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">
            <div>Director</div>
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          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
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          <td style="width: 29.13%; vertical-align: top;">
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          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top; border-bottom: #000000 2px solid;">&#160;/s/ Gustave J. Scacco<br>
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          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">
            <div>Director</div>
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          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top; border-bottom: 2px solid black;">
            <div style="text-align: center;">August 4, 2023</div>
          </td>
        </tr>
        <tr>
          <td style="width: 29.13%; vertical-align: top;">
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          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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          <td style="width: 29.13%; vertical-align: top;">&#160;</td>
          <td style="width: 5.48%; vertical-align: top;">&#160;</td>
          <td style="width: 30.8%; vertical-align: top;">&#160;</td>
          <td style="width: 5.46%; vertical-align: top;">&#160;</td>
          <td style="width: 29.12%; vertical-align: top;">&#160;</td>
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Registration No. 333-
As filed with the Securities and Exchange Commission on August 4, 2023
UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C.  20549
_________________________
FORM S-8
REGISTRATION STATEMENT
UNDER
THE SECURITIES ACT OF 1933
Orange County Bancorp, Inc.
(Exact Name of Registrant as Specified in its Charter)
Delaware
26-1135778
(State or Other Jurisdiction of
(I.R.S. Employer Identification No.)
Incorporation or Organization)
212 Dolson Avenue
Middletown, New York 10940
(Address of Principal Executive Offices)
Orange County Bancorp, Inc. 2023 Equity Incentive Plan
(Full Title of the Plan)
Copies to:
Michael J. Gilfeather
Benjamin M. Azoff, Esq.
President and Chief Executive Officer
Brendan M. Saxon, Esq.
Orange County Bancorp, Inc.
Luse Gorman, PC
212 Dolson Avenue
5335 Wisconsin Ave., N.W., Suite 780
Middletown, New York 10940
Washington, DC 20015-2035
(845) 341-5000
(202) 274-2000
(Name, Address and Telephone
Number of Agent for Service)
Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, smaller reporting company, or an emerging growth company. See the definitions of "large
      accelerated filer," "accelerated filer," "smaller reporting company" and "emerging growth company" in Rule 12b-2 of the Securities Exchange Act of 1934, as amended:
Large accelerated filer ☐
Accelerated filer ☐
Non-accelerated filer  ⌧
Smaller reporting company⌧
Emerging growth company ⌧
If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to
      Section 7(a)(2)(B) of the Securities Act. ☐
PART I.
INFORMATION

        REQUIRED IN THE SECTION 10(a) PROSPECTUS
Items 1 and 2.
Plan Information; and Registrant Information and Employee Plan Annual Information
The documents containing the information specified in Part I of Form S-8 have been or will be sent or given to participants in the Orange County Bancorp, Inc. 2023 Equity
      Incentive Plan (the "Plan") as specified by Rule 428(b)(1) promulgated by the Securities and Exchange Commission (the "Commission") under the Securities Act of 1933, as amended (the "Securities Act").
Such documents are not being filed with the Commission but constitute (along with the documents incorporated by reference into this Registration Statement pursuant to Item 3 of
      Part II hereof) a prospectus that meets the requirements of Section 10(a) of the Securities Act.
PART II.
INFORMATION

        REQUIRED IN THE REGISTRATION STATEMENT
Item 3.
Incorporation

        of Documents by Reference
The following documents previously filed by Orange County Bancorp, Inc. (the "Company") with the Commission under the Securities Exchange Act of 1934, as amended (the "Exchange
      Act"), are incorporated herein by reference (other than any such documents or portions thereof that are furnished under Item 2.02 or Item 7.01 of Form 8-K, unless otherwise indicated therein, including any exhibits included with such items):
(a)
The Company's Annual Report on Form 10-K for the year ended
      December 31, 2022, filed with the Commission on
March 24, 2023
(File No. 001-40711) pursuant to Section 13(a) of the Exchange Act
      (including information specifically incorporated by reference therein from the Company's definitive proxy statement on Schedule 14A, filed on
April
        14, 2023
);
(b)
The Company's Quarterly Report on Form 10-Q for the quarter
      ended March 31, 2023, filed with the Commission on
May 15, 2023
(File No. 001-40711);
(c)
The Company's Current Reports on Form 8-K filed with the
      Commission on
February 17, 2023
,
May

        19, 2023
,
May 24, 2023
, and
June

        26, 2023
(File No. 001-40711 for all); and
(d)
The description of the Company's common stock contained in
      the Registration Statement on Form 8-A, filed with the Commission on
August 4, 2021
,
to register the Company's
      common stock under the Exchange Act (File No. 000-40711), including any subsequent amendments or reports filed for the purpose of updating such description.
All documents subsequently filed by the Company with the Commission pursuant to Sections 13(a), 13(c), 14, or 15(d) of the Exchange Act, after the date hereof, and prior to the
      filing of a post-effective amendment which indicates that all securities offered hereby have been sold or which deregisters all securities then remaining unsold, shall be deemed incorporated by reference into this Registration Statement and to be a
      part thereof from the date of the filing of such documents.
Any statement contained in the documents incorporated, or deemed to be incorporated, by reference herein or therein shall be deemed to be modified or superseded for purposes of
      this Registration Statement and the prospectus to the extent that a statement contained herein or therein or in any other subsequently filed document which also is, or is deemed to be, incorporated by reference herein or therein modifies or
      supersedes such statement.  Any such statement so modified or superseded shall not be deemed, except as so modified or superseded, to constitute a part of this Registration Statement and the prospectus.
All information appearing in this Registration Statement and the prospectus is qualified in its entirety by the detailed information, including financial statements, appearing in
      the documents incorporated herein or therein by reference.
Item 4.  Description of Securities
Not applicable.
Item 5.  Interests of Named Experts and Counsel
None.
Item 6.  Indemnification of Directors and Officers
Article X of the Certificate of Incorporation and Article VI of the Bylaws of Orange County Bancorp, Inc. (the "Corporation") set forth circumstances under which directors, officers, employees and
        agents of the Corporation may be insured or indemnified against liability which they incur in their capacities as such:
ARTICLE X.  Limitation on Liability.
A director of the Corporation shall not be personally liable to the Corporation or its stockholders for monetary damages for breach of fiduciary duty as a director, except for
      liability: (i) for any breach of the director's duty of loyalty to the Corporation or its stockholders; (ii) for acts or omissions not in good faith or which involve intentional misconduct or a knowing violation of law; (iii) under Section 174 of the
      Delaware General Corporation Law; or (iv) for any transaction from which the director derived an improper personal benefit. If the Delaware General Corporation Law is amended to authorize corporate action further eliminating or limiting the personal
      liability of directors, then the liability of a director of the Corporation shall be eliminated or limited to the fullest extent permitted by the Delaware General Corporation Law, as so amended.
Any repeal or modification of the foregoing paragraph by the stockholders of the Corporation shall not adversely affect any right or protection of a director of the Corporation
      existing at the time of such repeal or modification.
ARTICLE VI. Indemnification
Section 1. Actions, Suits or Proceedings Other Than Those by or in the Right of the Corporation. Subject to Section 3 of this Article VI, the Corporation shall indemnify any
      person who was or is a party or is threatened to be made a party to any threatened, pending or completed action, suit or proceeding, whether civil, criminal, administrative or investigative (other than an action by or in the right of the Corporation)
      by reason of the fact that the person is or was or has agreed to become a director or officer of the Corporation, or is or was a director or officer of the Corporation serving at the request of the Corporation as a director, officer, employee or
      agent of another corporation, partnership, joint venture, trust, employee benefit plan or other enterprise, against expenses (including attorney's fees), judgments, fines and amounts paid in settlement actually and reasonably incurred by the person
      in connection with such action, suit or proceeding if the person acted in good faith and in a manner the person reasonably believed to be in or not opposed to the best interests of the Corporation, and, with respect to any criminal action or
      proceeding, had no reasonable cause to believe the person's conduct was unlawful. The termination of any action, suit or proceeding by judgment, order, settlement, conviction, or upon a plea of nolo contendere or its equivalent, shall not, of itself,
      create a presumption that the person did not act in good faith and in a manner which the person reasonably believed to be in or not opposed to the best interests of the corporation, and, with respect to criminal action or proceeding, had reasonable
      cause to believe that the person's conduct was unlawful.
Section 2. Actions, Suits or Proceedings by or in the Right of the Corporation. Subject to Section 3 of this Article VI, the Corporation shall indemnify any person who was or is
      a party or is threatened to be made a party to any threatened, pending or completed action or suit by or in the right of the Corporation to procure a judgment in its favor by reason of the fact that he is or was a director or officer of the
      Corporation, or is or was a director or officer of the Corporation serving at the request of the Corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust, employee benefit plan or other
      enterprise against expenses (including attorneys' fees) actually and reasonably incurred by him in connection with the defense or settlement of such action or suit if he acted in good faith and in a manner he reasonably believed to be in or not
      opposed to the best interests of the Corporation; except that no indemnification shall be made in respect of any claim, issue or matter as to which such person shall have been adjudged to be liable to the Corporation unless and only to the extent
      that the Court of Chancery or the court in which such action or suit was brought shall determine upon application that, despite the adjudication of liability but in view of all the circumstances of the case, such person is fairly and reasonably
      entitled to indemnity for such expenses which the Court of Chancery or such other court shall deem proper.
2
Section 3. Authorization of Indemnification. Any indemnification under this Article VI (unless ordered by a court) shall be made by the Corporation only as authorized in the
      specific case upon a determination that indemnification of the present or former director or officer is proper in the circumstances because he or she has met the applicable standard of conduct set forth in Section 1 or Section 2 of this Article VI,
      as the case may be. Such determination shall be made (i) by the Board by a majority vote of directors who were not parties to such action, suit or proceeding, even though less than a quorum, (ii) by a committee of such directors designated by
      majority vote of such directors, even though less than a quorum; (iii) if there are no such directors, or if such directors so direct, by independent legal counsel in a written opinion, or (iv) by the stockholders. To the extent, however, that a
      director or officer of the Corporation has been successful on the merits or otherwise in defense of any action, suit or proceeding described above, or in defense of any claim, issue or matter therein, he or she shall be indemnified against expenses
      (including attorneys' fees) actually and reasonably incurred by him or her in connection therewith, without the necessity of authorization in the specific case.
Section 4. Indemnification by a Court. Notwithstanding any contrary determination in the specific case under Section 3 of this Article VI, and notwithstanding the absence of any
      determination thereunder, any director or officer may apply to any court of competent jurisdiction in the State of Delaware for indemnification to the extent otherwise permissible under Sections 1 and 2 of this Article VI. The basis of such
      indemnification by a court shall be a determination by such court that indemnification of the director or officer is proper in the circumstances because he or she has met the applicable standards of conduct set forth in Sections 1 or 2 of this
      Article VI, as the case may be. Neither a contrary determination in the specific case under Section 3 of this Article VI nor the absence of any determination thereunder shall be a defense to such application or create a presumption that the director
      or officer seeking indemnification has not met any applicable standard of conduct. Notice of any application for indemnification pursuant to this Section 4 shall be given to the Corporation promptly upon the filing of such application. If successful,
      in whole or in part, the director or officer seeking indemnification shall also be entitled to be paid the expense of prosecuting such application.
Section 5. Expenses Payable in Advance. Expenses incurred by a director or officer in defending or investigating a threatened or pending action, suit or proceeding shall be paid
      by the Corporation in advance of the final disposition of such action, suit or proceeding upon receipt of an undertaking by or on behalf of such director or officer to repay such amount if it shall ultimately be determined that he or she is not
      entitled to be indemnified by the Corporation as authorized in this Article VI.
Section 6. Nonexclusivity of Indemnification and Advancement of Expenses. The indemnification and advancement of expenses provided by or granted pursuant to this Article VI shall
      not be deemed exclusive of any other rights to which those seeking indemnification or advancement of expenses may be entitled under any Bylaws, agreement, contract, vote of stockholders or disinterested directors or pursuant to the direction (however
      embodied) of any court of competent jurisdiction or otherwise, both as to action in his or her official capacity and as to action in another capacity while holding such office, it being the policy of the Corporation that indemnification of the
      persons specified in Sections I and 2 of this Article VI shall be made to the fullest extent permitted by law. The provisions of this Article VI shall not be deemed to preclude the indemnification of any person who is not specified in Sections I or 2
      of this Article VI but whom the Corporation has the power or obligation to indemnify under the provisions of the Delaware General Corporation Law or otherwise.
Section 7. Insurance. The Corporation may purchase and maintain insurance on behalf of any person who is or was a director or officer of the Corporation, or is or was a director
      or officer of the Corporation serving at the request of the Corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust, employee benefit plan or other enterprise against any liability asserted
      against him or her and incurred by him or her in any such capacity, or arising out of his or her status as such, whether or not the Corporation would have the power or the obligation to indemnify him or her against such liability under the provisions
      of this Article VI.
Section 8. Certain Definitions. For purposes of this Article VI, references to "the Corporation" shall include, in addition to the resulting corporation, any constituent
      corporation (including any constituent of a constituent) absorbed in a consolidation or merger which, if its separate existence had continued, would have had power and authority to indemnify its directors or officers, so that any person who is or was
      a director or officer of such constituent corporation, or is or was a director or officer of such constituent corporation serving at the request of such constituent corporation as a director, officer, employee or agent of another corporation,
      partnership, joint venture, trust, employee benefit plan or other enterprise, shall stand in the same position under the provisions of this Article VI with respect to the resulting or surviving corporation as he or she would have with respect to such
      constituent corporation if its
3
separate existence had continued. For purposes of this Article VI, references to "fines" shall include any excise taxes assessed on a person with respect to an employee benefit plan; and references
      to "serving at the request of the Corporation" shall include any service as a director, officer, employee or agent of the Corporation which imposes duties on, or involves services by, such director or officer with respect to an employee benefit plan,
      its participants or beneficiaries; and a person who acted in good faith and in a manner he reasonably believed to be in the interest of the participants and beneficiaries of an employee benefit plan shall be deemed to have acted in a manner "not
      opposed to the best interests of the Corporation" as referred to in this Article VI.
Section 9. Survival of Indemnification and Advancement of Expenses. The indemnification and advancement of expenses provided by, or granted pursuant to, this Article VI shall,
      unless otherwise provided when authorized or ratified, continue as to a person who has ceased to be a director or officer and shall inure to the benefit of the heirs, executors and administrators of such a person.
Section 10. Limitation on Indemnification. Notwithstanding anything contained in this Article VI to the contrary, except for proceedings to enforce rights to indemnification
      (which shall be governed by Section 4 hereof), the Corporation shall not be obligated to indemnify any director or officer in connection with a proceeding (or part thereof) initiated by such person unless such proceeding (or part thereof) was
      authorized or consented to by the Board of the Corporation.
Section 11. Indemnification of Employees and Agents. The Corporation may, to the extent authorized from time to time by the Board, provide rights to indemnification and to the
      advancement of expenses to employees and agents of the Corporation similar to those conferred in this Article VI to directors and officers of the Corporation.
Item 7.  Exemption From Registration Claimed.
Not applicable.
Item 8.  List of Exhibits.
Regulation S-K
Exhibit Number
Document
4
Form of Common Stock Certificate (incorporated by reference to Exhibit 4.1 to the Registration Statement on
                Form S-1 (File No. 333-257781), as amended, filed by the Company under the Securities Act with the Commission on July 9, 2021)
5
Opinion of Luse Gorman, PC
10.1
Orange County Bancorp, Inc. 2023 Equity Incentive Plan (incorporated by reference to Appendix A to the proxy
                statement for the Annual Meeting of Shareholders of Orange County Bancorp, Inc., filed under the Exchange Act on April 14, 2023 (File No. 001-40711))
10.2
Form of Restricted Stock Unit Agreement (Non-Employee Directors)
10.3
Form of Restricted Stock Unit Agreement (Employee/Consultants)
10.4
Form of Performance Restricted Stock Unit Agreement (Employee)
23.1
Consent of Luse Gorman, PC (contained in Exhibit 5)
23.2
Consent of Crowe LLP (Independent Registered Public Accounting Firm)
24
Power of Attorney (contained on signature page)
107
Filing Fee Table
4
Item 9.
Undertakings
The undersigned registrant hereby undertakes:
1.
To file, during any period in which offers or sales are
      being made, a post-effective amendment to the Registration Statement:
(i)
to include any prospectus required by Section 10(a)(3) of
      the Securities Act;
(ii)
to reflect in the prospectus any facts or events arising
      after the effective date of the registration statement (or the most recent post-effective amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set forth in the registration statement. 
      Notwithstanding the foregoing, any increase or decrease in volume of securities offered (if the total dollar value of securities offered would not exceed that which was registered) and any deviation from the low or high end of the estimated maximum
      offering range may be reflected in the form of prospectus filed with the Commission pursuant to Rule 424(b) (section 230.424(b)) if, in the aggregate, the changes in volume and price represent no more than 20% change in the maximum aggregate offering
      price set forth in the "Calculation of Registration Fees" table in the effective registration statement;
(iii)
to include any material information with respect to the
      plan of distribution not previously disclosed in this Registration Statement or any material change to such information in this Registration Statement;
provided, however, that paragraphs 1(i) and 1(ii) above do not apply if the information required to be included in a post-effective amendment by these paragraphs is contained in reports filed with
      or furnished to the Commission by the Company pursuant to Section 13 or Section 15(d) of the Exchange Act that are incorporated by reference in this Registration Statement.
2.
That, for the purpose of determining any liability under the
      Securities Act, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial
bona fide
offering thereof;
3.
To remove from registration by means of a post-effective
      amendment any of the securities being registered which remain unsold at the termination of the offering;
4.
That, for purposes of determining any liability under the
      Securities Act, each filing of the registrant's annual report pursuant to Section 13(a) or 15(d) of the Exchange Act (and, where applicable, each filing of an employee benefit plan's annual report pursuant to Section 15(d) of the Exchange Act) that
      is incorporated by reference in the registration statement shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide
      offering thereof; and
5.
Insofar as indemnification for liabilities arising under the
      Securities Act may be permitted to directors, officers and controlling persons of the registrant pursuant to the foregoing provisions, or otherwise, the registrant has been advised that in the opinion of the Commission such indemnification is against
      public policy as expressed in the Securities Act and is, therefore, unenforceable.  In the event that a claim for indemnification against such liabilities (other than the payment by the registrant of expenses incurred or paid by a director, officer
      or controlling person of the registrant in the successful defense of any action, suit or proceeding) is asserted by such director, officer or controlling person in connection with the securities being registered, the registrant will, unless in the
      opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question whether such indemnification by it is against public policy as expressed in the Securities Act and will be
      governed by the final adjudication of such issue.
5
SIGNATURES
The Registrant.
Pursuant to the requirements of the Securities Act of 1933, as amended, the Registrant certifies that it has reasonable grounds to believe
      that it meets all of the requirements for filing on Form S-8 and has duly caused this Registration Statement on Form S-8 to be signed on its behalf by the undersigned, thereunto duly authorized, in the City of Middletown, State of New York, on August
      4, 2023.
ORANGE COUNTY BANCORP, INC.
By:
/s/ Michael J. Gilfeather
Michael J. Gilfeather
President and Chief Executive Officer
(Duly Authorized Representative)
POWER OF ATTORNEY
We, the undersigned directors and officers of Orange County Bancorp, Inc. (the "Company") hereby severally constitute and appoint Michael J. Gilfeather, as our true and lawful
      attorney and agent, to do any and all things in our names in the capacities indicated below which said Michael J. Gilfeather may deem necessary or advisable to enable the Company to comply with the Securities Act of 1933, as amended, and any rules,
      regulations and requirements of the Securities and Exchange Commission, in connection with the registration of shares of Company common stock to be granted and shares of Company common stock to be issued upon the exercise of stock options to be
      granted under the Orange County Bancorp, Inc. 2023 Equity Incentive Plan, including specifically, but not limited to, power and authority to sign for us in our names in the capacities indicated below the registration statement and any and all
      amendments (including post-effective amendments) thereto; and we hereby approve, ratify and confirm all that said Michael J. Gilfeather shall do or cause to be done by virtue thereof.
Pursuant to the requirements of the Securities Act, this registration statement has been signed by the following persons in the capacities and on the date indicated.
Signatures
Title
Date
/s/ Michael J. Gilfeather
President and Chief
August 4, 2023
Michael J. Gilfeather
Executive Officer
(Principal Executive Officer)
/s/ Michael Lesler
Senior Vice President and Chief
August 4, 2023
Michael Lesler
Financial Officer (Principal
Financial and Accounting Officer)
/s/ Jonathan F. Rouis
Chairman of the Board
August 4, 2023
Jonathan F. Rouis
/s/ Louis Heimbach
Director
August 4, 2023
Louis Heimbach
/s/ Gregory F. Holcombe
Director
August 4, 2023
Gregory F. Holcombe
6
Signatures
Title
Date
/s/ Kevin J. Keane
Director
August 4, 2023
Kevin J. Keane
/s/ Marianna R. Kennedy
Director
August 4, 2023
Marianna R. Kennedy
/s/ William D. Morrison
Director
August 4, 2023
William D. Morrison
/s/ Richard B. Rowley
Director
August 4, 2023
Richard B. Rowley
/s/ Terry R. Saturno
Director
August 4, 2023
Terry R. Saturno
/s/ Gustave J. Scacco
Director
August 4, 2023
Gustave J. Scacco
7