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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: right">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: right">As filed with the Securities and Exchange
Commission on October 31, 2023</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: right">SEC Registration No. 333-</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: right">&nbsp;</P>

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<P STYLE="font: 14pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>UNITED STATES</B></P>

<P STYLE="font: 14pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>SECURITIES AND EXCHANGE COMMISSION</B></P>

<P STYLE="font: 12pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Washington, D.C. 20549</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 18pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>FORM S-8</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 12pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>REGISTRATION STATEMENT</B></P>

<P STYLE="font: 12pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>UNDER</B></P>

<P STYLE="font: 12pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>THE SECURITIES ACT OF 1933</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 24pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>TOMPKINS FINANCIAL CORPORATION</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Exact name of registrant as specified in
its charter)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>NEW YORK</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(State or other jurisdiction of incorporation
or organization)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>16-1482357</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(I.R.S. Employer Identification No.)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>118 E. Seneca Street, P.O. Box 460</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Ithaca, New York 14851</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Address of Principal Executive Offices)
(Zip Code)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 40.1pt 0pt 34.55pt; text-align: center"><B>2019 EQUITY INCENTIVE
PLAN</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Full title of the plan)</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; border-collapse: collapse">
<TR STYLE="vertical-align: bottom">
    <TD STYLE="width: 48%">&nbsp;</TD>
    <TD STYLE="width: 5%">&nbsp;</TD>
    <TD STYLE="width: 47%">&nbsp;</TD></TR>
<TR>
    <TD STYLE="vertical-align: top; text-align: center"><B>Matthew D. Tomazin</B></TD>
    <TD STYLE="vertical-align: bottom">&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center"><B>&nbsp;with a copy to:</B></TD></TR>
<TR>
    <TD STYLE="vertical-align: top; text-align: center"><B>Executive Vice President, Chief Financial Officer</B></TD>
    <TD STYLE="vertical-align: bottom">&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center"><B>Alyssa H. Fontaine</B></TD></TR>
<TR>
    <TD STYLE="vertical-align: top; text-align: center"><B>Tompkins Financial Corporation</B></TD>
    <TD STYLE="vertical-align: bottom">&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center"><B>Executive Vice President, General Counsel, and</B></TD></TR>
<TR>
    <TD STYLE="vertical-align: top; text-align: center"><B>P.O. Box 460</B></TD>
    <TD STYLE="vertical-align: bottom">&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center"><B>Chief Risk Officer</B></TD></TR>
<TR>
    <TD STYLE="vertical-align: top; text-align: center"><B>Ithaca, New York 14851</B></TD>
    <TD STYLE="vertical-align: bottom">&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center"><B>Tompkins Financial Corporation</B></TD></TR>
<TR>
    <TD STYLE="vertical-align: top; text-align: center">&nbsp;</TD>
    <TD STYLE="vertical-align: bottom">&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center"><B>P.O. Box 460</B></TD></TR>
<TR>
    <TD STYLE="vertical-align: top; text-align: center">&nbsp;</TD>
    <TD STYLE="vertical-align: bottom">&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center"><B>Ithaca, New York 14851</B></TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;(Name and Address of Agent For Service)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; border-collapse: collapse">
<TR STYLE="vertical-align: top">
    <TD STYLE="width: 100%">
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>(607) 274-7685</B></P></TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Telephone number, including area code,
of agent for service)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">Indicate by check mark whether the registrant
is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth
company. See the definitions of &ldquo;large accelerated filer,&rdquo; &ldquo;accelerated filer,&rdquo; &ldquo;non-accelerated
filer,&rdquo; &ldquo;smaller reporting company,&rdquo; and emerging growth company&rdquo; in Rule 12b-2 of the Exchange Act. (Check
one):</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; border-collapse: collapse">
<TR STYLE="vertical-align: top">
    <TD STYLE="width: 18%; padding-right: 5.4pt; padding-left: 5.4pt; text-align: left">Large accelerated filer</TD>
    <TD STYLE="width: 32%; padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9746;</FONT></TD>
    <TD STYLE="width: 23%; padding-right: 5.4pt; padding-left: 5.4pt; text-align: left">Accelerated filer</TD>
    <TD STYLE="width: 27%; padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: left">Non-accelerated filer</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: left">Smaller reporting company</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></TD></TR>
<TR STYLE="vertical-align: top">
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: left">Emerging Growth Company</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></TD></TR>
<TR STYLE="vertical-align: top">
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: justify">&nbsp;</TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">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.&nbsp;<FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>




<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>EXPLANATORY NOTE</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">This Registration Statement on Form S-8
(this &ldquo;Registration Statement&rdquo;) is being filed by Tompkins Financial Corporation (the &ldquo;Company,&rdquo; &ldquo;Registrant,&rdquo;
&ldquo;we,&rdquo; &ldquo;us&rdquo; or &ldquo;our&rdquo;) to register an additional 1,000,000 shares of common stock for issuance
under the Tompkins Financial Corporation 2019 Equity Incentive Plan, as amended (the &ldquo;Plan&rdquo;). The Plan was amended
on April 27, 2023 to increase the number of shares of common stock authorized for issuance pursuant to the Plan by 1,000,000 shares.
Pursuant to General Instruction E of Form S-8, this Registration Statement incorporates by reference the contents of the Registrant&rsquo;s
previous Registration Statement on Form S-8 (No. 333-231413) filed with the Securities and Exchange Commission (the &ldquo;Commission&rdquo;)
on May 13, 2019, except as modified herein.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>PART II</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>INFORMATION REQUIRED IN THE REGISTRATION
STATEMENT</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><B>Item 3. Incorporation of Documents by Reference.</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">The following documents that the Registrant has filed with the
Commission under the Securities Exchange Act of 1934 (the &ldquo;Exchange Act&rdquo;) are incorporated by reference into this Registration
Statement:</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.25in"></TD><TD STYLE="width: 0.25in">(a)</TD><TD>the Company&rsquo;s Annual Report on Form 10-K for the fiscal year ended December 31, 2022;</TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif"></P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.25in"></TD><TD STYLE="width: 0.25in">(b)</TD><TD>the Company&rsquo;s Quarterly Reports on Form 10-Q for the fiscal quarters ended March 31, 2023 and June 30, 2023;</TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif"></P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.25in"></TD><TD STYLE="width: 0.25in">(c)</TD><TD>the Company&rsquo;s Current Reports on Form 8-K to the extent filed and not furnished with the Commission on January 27, 2023,
April 28, 2023, May 3, 2023, May 9, 2023, May 11, 2023, July 12, 2023, July 21, 2023, September 18, 2023, September 29, 2023, and
October 27, 2023;</TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif"></P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.25in"></TD><TD STYLE="width: 0.25in">(d)</TD><TD>The description of the Common Stock of the Registrant included as Exhibit 4.2 to the Registrant&rsquo;s Annual Report on Form
10-K for the fiscal year ended December 31, 2019 and filed with the Commission on March 2, 2020.</TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">In addition, all reports and other documents subsequently filed
(but not furnished) by the Registrant pursuant to Sections 13(a), 14 and 15(d) of the Exchange Act, prior to the filing of a post-effective
amendment that indicates that all securities offered have been sold or that deregisters all securities then remaining unsold, shall
be deemed to be incorporated by reference in this Registration Statement and to be a part hereof from the date of filing of such
documents with the Commission. Any statement contained in a document incorporated or deemed to be incorporated by reference in
this Registration Statement shall be deemed to be modified or superseded for purposes of this Registration Statement to the extent
that a statement contained in this Registration Statement, or in any other subsequently filed document that also is or is deemed
to be incorporated by reference in this Registration Statement, modifies or supersedes such prior statement. Any statement contained
in this Registration Statement shall be deemed to be modified or superseded to the extent that a statement contained in a subsequently
filed document that is or is deemed to be incorporated by reference in this Registration Statement modifies or supersedes such
prior statement. Any statement so modified or superseded shall not be deemed, except as so modified or superseded, to constitute
a part of this Registration Statement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">No document or information deemed to be furnished and not filed
in accordance with rules of the Commission shall be deemed to be incorporated herein by reference unless such document or information
expressly provides to the contrary.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><B>Item 8. Exhibits.</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">The following exhibits are filed with this Registration Statement:</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; border-collapse: collapse">
<TR STYLE="vertical-align: top">
    <TD STYLE="width: 8%"><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000101905608001017/ex3_ii.htm">4.1</A></TD>
    <TD STYLE="width: 92%"><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000101905608001017/ex3_ii.htm">Amended and Restated Certificate of Incorporation of the Company, incorporated herein by reference to Exhibit 3(i) to the Company&rsquo;s Form 10-Q, filed with the Commission on August 11, 2008.</A></TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000101905611000117/ex3_1.htm">4.2</A></TD>
    <TD><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000101905611000117/ex3_1.htm">Second Amended and Restated Bylaws of the Company, incorporated herein by reference to Exhibit 3.1 to the Company&rsquo;s Current Report on Form 8-K, filed with the Commission on January 31, 2011.</A></TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>4.3</TD>
    <TD>Form of Specimen Common Stock Certificate of the Company, incorporated herein by reference to Exhibit 4 to the Company&rsquo;s Registration Statement on Form 8-A (No. 0-27514), filed with the Commission on December 29, 1995.</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000100581720000005/exhibit42-12312019.htm">4.4</A></TD>
    <TD><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000100581720000005/exhibit42-12312019.htm">Description of Securities Registered Under Section 12 of the Exchange Act, incorporated herein by reference to Exhibit 4.2 to the Company's Annual Report on Form 10-K, filed with the Commission on March 2, 2020.</A></TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000138713119002241/tmp-def14a_050719.htm">4.5</A></TD>
    <TD><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000138713119002241/tmp-def14a_050719.htm">Tompkins Financial Corporation 2019 Equity Incentive Plan, incorporated herein by reference to Appendix A of the Company&rsquo;s DEF 14A filed with the commission on March 29, 2019.</A></TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000100581723000009/tmp2023-06x30ex101.htm">4.6</A></TD>
    <TD><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000100581723000009/tmp2023-06x30ex101.htm">Amendment No. 1 to the Tompkins Financial Corporation 2019 Equity Incentive Plan, incorporated herein by reference to Exhibit 10.1 to the Company&rsquo;s Quarterly Report on Form 10-Q filed with the Commission on August 9, 2023.</A></TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD><A HREF="ex5-1.htm">5*</A></TD>
    <TD><A HREF="ex5-1.htm">Opinion of Holland &amp; Knight LLP</A></TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD><A HREF="ex23-1.htm">23.1*</A></TD>
    <TD><A HREF="ex23-1.htm">Consent of KPMG LLP, Independent Registered Public Accounting Firm</A></TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD><A HREF="ex5-1.htm">23.2*</A></TD>
    <TD><A HREF="ex5-1.htm">Consent of Holland &amp; Knight LLP (included in Exhibit 5)</A></TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD><A HREF="#a001">24*</A></TD>
    <TD><A HREF="#a001">Power of Attorney (included at pages II-3 and II-4)</A></TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD><A HREF="ex107.htm">107*</A></TD>
    <TD><A HREF="ex107.htm">Filing Fee Table</A></TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">*filed herewith</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>SIGNATURES</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Pursuant to the requirements of the Securities
Act of 1933, 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 to be signed on its behalf by the undersigned, thereunto duly authorized,
in the City of Ithaca, state of New York, on this 31<SUP>st</SUP> day of October, 2023.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%; border-collapse: collapse">
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD COLSPAN="2">TOMPKINS FINANCIAL CORPORATION</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="width: 60%">&nbsp;</TD>
    <TD STYLE="width: 6%">&nbsp;</TD>
    <TD STYLE="width: 34%">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>By:</TD>
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Stephen S. Romaine</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>Stephen S. Romaine</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>President and Chief Executive Officer </TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B><A NAME="a001"></A>POWER OF ATTORNEY</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">KNOW ALL PERSONS BY THESE PRESENTS, that
each person whose signature appears below constitutes and appoints, jointly and severally, Stephen S. Romaine and Matthew D. Tomazin
and each of them, as their true and lawful attorneys-in-fact and agents, each with full power of substitution, for them, and in
their name, place and stead, and in any and all capacities, to sign any and all amendments (including post-effective amendments)
to this Registration Statement on Form S-8, and to file the same, with all exhibits thereto and other documents in connection therewith,
with the Securities and Exchange Commission, granting unto said attorneys-in-fact and agents, and each of them, full power and
authority to do and perform each and every act and thing requisite or necessary to be done as fully to all intents and purposes
as they might or could do in person, hereby ratifying and confirming all that said attorneys-in-fact and agents, or any of them,
or their substitutes, may lawfully do or cause to be done by virtue hereof.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Pursuant to the requirements of the Securities
Exchange Act of 1933, this Registration Statement and Power of Attorney have been signed below by the following persons in the
capacities and on the dates indicated:</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; border-collapse: collapse">
<TR STYLE="vertical-align: top">
    <TD STYLE="width: 25%"><B>Name</B></TD>
    <TD STYLE="width: 5%">&nbsp;</TD>
    <TD STYLE="width: 45%"><B>Capacity</B></TD>
    <TD STYLE="width: 5%">&nbsp;</TD>
    <TD STYLE="width: 20%"><B>Date</B></TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Stephen S. Romaine</TD>
    <TD>&nbsp;</TD>
    <TD ROWSPAN="2">President and Chief Executive Officer, Director <BR>
(Principal Executive Officer) </TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Stephen S. Romaine</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Matthew D. Tomazin</TD>
    <TD>&nbsp;</TD>
    <TD ROWSPAN="2">Executive Vice President, Chief Financial Officer <BR>
(Principal Financial Officer)</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Matthew D. Tomazin</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ David Kershaw</TD>
    <TD>&nbsp;</TD>
    <TD ROWSPAN="2">Senior Vice President, Chief Accounting Officer <BR>
(Principal Accounting Officer)</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>David Kershaw</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Thomas R. Rochon </TD>
    <TD>&nbsp;</TD>
    <TD>Chair of the Board </TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Thomas R. Rochon</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ James W. Fulmer</TD>
    <TD>&nbsp;</TD>
    <TD>Vice Chair, Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>James W. Fulmer</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
</TABLE>

<P STYLE="margin: 0">&nbsp;</P>

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<P STYLE="margin: 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; border-collapse: collapse">
<TR STYLE="vertical-align: top">
    <TD STYLE="width: 25%">&nbsp;</TD>
    <TD STYLE="width: 5%">&nbsp;</TD>
    <TD STYLE="width: 45%">&nbsp;</TD>
    <TD STYLE="width: 5%">&nbsp;</TD>
    <TD STYLE="width: 20%">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ John E. Alexander</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>John E. Alexander</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Paul J. Battaglia</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Paul J. Battaglia</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Nancy E. Catarisano</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Nancy E. Catarisano</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Daniel J. Fessenden</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Daniel J. Fessenden</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Patricia A.&nbsp;&nbsp;Johnson</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Patricia A. Johnson</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Angela B. Lee</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Angela B. Lee</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ John D. McClurg</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>John D. McClurg</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Ita M. Rahilly</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Ita. M. Rahilly</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Michael H. Spain</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Michael H. Spain</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Jennifer R. Tegan</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Jennifer R. Tegan</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Alfred J. Weber</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>&nbsp;</TD>
    <TD>October 31, 2023</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Alfred J. Weber</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
</TABLE>


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[{"type": "S-8", "sequence": "1", "filename": "tmp-s8_103023.htm", "description": "INITIAL REGISTRATION STATEMENT", "secsgml_size_bytes": 36589}]
{"company-data": {"conformed-name": "TOMPKINS FINANCIAL CORP", "cik": "0001005817", "assigned-sic": "6022", "irs-number": "161482357", "state-of-incorporation": "NY", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-275236", "film-number": "231365158"}, "business-address": {"street1": "118 E SENECA STREET", "street2": "P.O. BOX 460", "city": "ITHACA", "state": "NY", "zip": "14850", "phone": "607-274-2078"}, "mail-address": {"street1": "118 E. SENECA STREET", "street2": "PO BOX 460", "city": "ITHACA", "state": "NY", "zip": "14850"}, "former-company": [{"former-conformed-name": "TOMPKINS TRUSTCO INC", "date-changed": "19990512"}, {"former-conformed-name": "TOMPKINS COUNTY TRUSTCO INC", "date-changed": "19960117"}]}
As filed with the Securities and Exchange
Commission on October 31, 2023
SEC Registration No. 333-
UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
FORM S-8
REGISTRATION STATEMENT
UNDER
THE SECURITIES ACT OF 1933
TOMPKINS FINANCIAL CORPORATION
(Exact name of registrant as specified in
its charter)
NEW YORK
(State or other jurisdiction of incorporation
or organization)
16-1482357
(I.R.S. Employer Identification No.)
118 E. Seneca Street, P.O. Box 460
Ithaca, New York 14851
(Address of Principal Executive Offices)
(Zip Code)
2019 EQUITY INCENTIVE
PLAN
(Full title of the plan)
Matthew D. Tomazin
with a copy to:
Executive Vice President, Chief Financial Officer
Alyssa H. Fontaine
Tompkins Financial Corporation
Executive Vice President, General Counsel, and
P.O. Box 460
Chief Risk Officer
Ithaca, New York 14851
Tompkins Financial Corporation
P.O. Box 460
Ithaca, New York 14851
(Name and Address of Agent For Service)
(607) 274-7685
(Telephone number, including area code,
of agent for service)
Indicate by check mark whether the registrant
is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth
company. See the definitions of "large accelerated filer," "accelerated filer," "non-accelerated
filer," "smaller reporting company," and emerging growth company" in Rule 12b-2 of the Exchange Act. (Check
one):
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.
☐
EXPLANATORY NOTE
This Registration Statement on Form S-8
(this "Registration Statement") is being filed by Tompkins Financial Corporation (the "Company," "Registrant,"
"we," "us" or "our") to register an additional 1,000,000 shares of common stock for issuance
under the Tompkins Financial Corporation 2019 Equity Incentive Plan, as amended (the "Plan"). The Plan was amended
on April 27, 2023 to increase the number of shares of common stock authorized for issuance pursuant to the Plan by 1,000,000 shares.
Pursuant to General Instruction E of Form S-8, this Registration Statement incorporates by reference the contents of the Registrant's
previous Registration Statement on Form S-8 (No. 333-231413) filed with the Securities and Exchange Commission (the "Commission")
on May 13, 2019, except as modified herein.
PART II
INFORMATION REQUIRED IN THE REGISTRATION
STATEMENT
Item 3. Incorporation of Documents by Reference.
The following documents that the Registrant has filed with the
Commission under the Securities Exchange Act of 1934 (the "Exchange Act") are incorporated by reference into this Registration
Statement:
(a)
the Company's Annual Report on Form 10-K for the fiscal year ended December 31, 2022;
(b)
the Company's Quarterly Reports on Form 10-Q for the fiscal quarters ended March 31, 2023 and June 30, 2023;
(c)
the Company's Current Reports on Form 8-K to the extent filed and not furnished with the Commission on January 27, 2023,
April 28, 2023, May 3, 2023, May 9, 2023, May 11, 2023, July 12, 2023, July 21, 2023, September 18, 2023, September 29, 2023, and
October 27, 2023;
(d)
The description of the Common Stock of the Registrant included as Exhibit 4.2 to the Registrant's Annual Report on Form
10-K for the fiscal year ended December 31, 2019 and filed with the Commission on March 2, 2020.
In addition, all reports and other documents subsequently filed
(but not furnished) by the Registrant pursuant to Sections 13(a), 14 and 15(d) of the Exchange Act, prior to the filing of a post-effective
amendment that indicates that all securities offered have been sold or that deregisters all securities then remaining unsold, shall
be deemed to be incorporated by reference in this Registration Statement and to be a part hereof from the date of filing of such
documents with the Commission. Any statement contained in a document incorporated or deemed to be incorporated by reference in
this Registration Statement shall be deemed to be modified or superseded for purposes of this Registration Statement to the extent
that a statement contained in this Registration Statement, or in any other subsequently filed document that also is or is deemed
to be incorporated by reference in this Registration Statement, modifies or supersedes such prior statement. Any statement contained
in this Registration Statement shall be deemed to be modified or superseded to the extent that a statement contained in a subsequently
filed document that is or is deemed to be incorporated by reference in this Registration Statement modifies or supersedes such
prior statement. Any statement so modified or superseded shall not be deemed, except as so modified or superseded, to constitute
a part of this Registration Statement.
No document or information deemed to be furnished and not filed
in accordance with rules of the Commission shall be deemed to be incorporated herein by reference unless such document or information
expressly provides to the contrary.
II-
1
Item 8. Exhibits.
The following exhibits are filed with this Registration Statement:
4.1
Amended and Restated Certificate of Incorporation of the Company, incorporated herein by reference to Exhibit 3(i) to the Company's Form 10-Q, filed with the Commission on August 11, 2008.
4.2
Second Amended and Restated Bylaws of the Company, incorporated herein by reference to Exhibit 3.1 to the Company's Current Report on Form 8-K, filed with the Commission on January 31, 2011.
4.3
Form of Specimen Common Stock Certificate of the Company, incorporated herein by reference to Exhibit 4 to the Company's Registration Statement on Form 8-A (No. 0-27514), filed with the Commission on December 29, 1995.
4.4
Description of Securities Registered Under Section 12 of the Exchange Act, incorporated herein by reference to Exhibit 4.2 to the Company's Annual Report on Form 10-K, filed with the Commission on March 2, 2020.
4.5
Tompkins Financial Corporation 2019 Equity Incentive Plan, incorporated herein by reference to Appendix A of the Company's DEF 14A filed with the commission on March 29, 2019.
4.6
Amendment No. 1 to the Tompkins Financial Corporation 2019 Equity Incentive Plan, incorporated herein by reference to Exhibit 10.1 to the Company's Quarterly Report on Form 10-Q filed with the Commission on August 9, 2023.
5*
Opinion of Holland & Knight LLP
23.1*
Consent of KPMG LLP, Independent Registered Public Accounting Firm
23.2*
Consent of Holland & Knight LLP (included in Exhibit 5)
24*
Power of Attorney (included at pages II-3 and II-4)
107*
Filing Fee Table
*filed herewith
II-
2
SIGNATURES
Pursuant to the requirements of the Securities
Act of 1933, 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 to be signed on its behalf by the undersigned, thereunto duly authorized,
in the City of Ithaca, state of New York, on this 31
st
day of October, 2023.
TOMPKINS FINANCIAL CORPORATION
By:
/s/ Stephen S. Romaine
Stephen S. Romaine
President and Chief Executive Officer
POWER OF ATTORNEY
KNOW ALL PERSONS BY THESE PRESENTS, that
each person whose signature appears below constitutes and appoints, jointly and severally, Stephen S. Romaine and Matthew D. Tomazin
and each of them, as their true and lawful attorneys-in-fact and agents, each with full power of substitution, for them, and in
their name, place and stead, and in any and all capacities, to sign any and all amendments (including post-effective amendments)
to this Registration Statement on Form S-8, and to file the same, with all exhibits thereto and other documents in connection therewith,
with the Securities and Exchange Commission, granting unto said attorneys-in-fact and agents, and each of them, full power and
authority to do and perform each and every act and thing requisite or necessary to be done as fully to all intents and purposes
as they might or could do in person, hereby ratifying and confirming all that said attorneys-in-fact and agents, or any of them,
or their substitutes, may lawfully do or cause to be done by virtue hereof.
Pursuant to the requirements of the Securities
Exchange Act of 1933, this Registration Statement and Power of Attorney have been signed below by the following persons in the
capacities and on the dates indicated:
Name
Capacity
Date
/s/ Stephen S. Romaine
President and Chief Executive Officer, Director
(Principal Executive Officer)
October 31, 2023
Stephen S. Romaine
/s/ Matthew D. Tomazin
Executive Vice President, Chief Financial Officer
(Principal Financial Officer)
October 31, 2023
Matthew D. Tomazin
/s/ David Kershaw
Senior Vice President, Chief Accounting Officer
(Principal Accounting Officer)
October 31, 2023
David Kershaw
/s/ Thomas R. Rochon
Chair of the Board
October 31, 2023
Thomas R. Rochon
/s/ James W. Fulmer
Vice Chair, Director
October 31, 2023
James W. Fulmer
II-
3
/s/ John E. Alexander
Director
October 31, 2023
John E. Alexander
/s/ Paul J. Battaglia
Director
October 31, 2023
Paul J. Battaglia
/s/ Nancy E. Catarisano
Director
October 31, 2023
Nancy E. Catarisano
/s/ Daniel J. Fessenden
Director
October 31, 2023
Daniel J. Fessenden
/s/ Patricia A.  Johnson
Director
October 31, 2023
Patricia A. Johnson
/s/ Angela B. Lee
Director
October 31, 2023
Angela B. Lee
/s/ John D. McClurg
Director
October 31, 2023
John D. McClurg
/s/ Ita M. Rahilly
Director
October 31, 2023
Ita. M. Rahilly
/s/ Michael H. Spain
Director
October 31, 2023
Michael H. Spain
/s/ Jennifer R. Tegan
Director
October 31, 2023
Jennifer R. Tegan
/s/ Alfred J. Weber
Director
October 31, 2023
Alfred J. Weber
II-
4