<SEC-DOCUMENT>0001387131-23-012956.txt : 20231031
<SEC-HEADER>0001387131-23-012956.hdr.sgml : 20231031
<ACCEPTANCE-DATETIME>20231031163241
ACCESSION NUMBER:		0001387131-23-012956
CONFORMED SUBMISSION TYPE:	S-8
PUBLIC DOCUMENT COUNT:		5
FILED AS OF DATE:		20231031
DATE AS OF CHANGE:		20231031
EFFECTIVENESS DATE:		20231031

FILER:

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			TOMPKINS FINANCIAL CORP
		CENTRAL INDEX KEY:			0001005817
		STANDARD INDUSTRIAL CLASSIFICATION:	STATE COMMERCIAL BANKS [6022]
		IRS NUMBER:				161482357
		STATE OF INCORPORATION:			NY
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		S-8
		SEC ACT:		1933 Act
		SEC FILE NUMBER:	333-275236
		FILM NUMBER:		231365158

	BUSINESS ADDRESS:	
		STREET 1:		118 E SENECA STREET
		STREET 2:		P.O. BOX 460
		CITY:			ITHACA
		STATE:			NY
		ZIP:			14850
		BUSINESS PHONE:		607-274-2078

	MAIL ADDRESS:	
		STREET 1:		118 E. SENECA STREET
		STREET 2:		PO BOX 460
		CITY:			ITHACA
		STATE:			NY
		ZIP:			14850

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	TOMPKINS TRUSTCO INC
		DATE OF NAME CHANGE:	19990512

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	TOMPKINS COUNTY TRUSTCO INC
		DATE OF NAME CHANGE:	19960117
</SEC-HEADER>
<DOCUMENT>
<TYPE>S-8
<SEQUENCE>1
<FILENAME>tmp-s8_103023.htm
<DESCRIPTION>INITIAL REGISTRATION STATEMENT
<TEXT>
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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: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: right">&nbsp;</P>

<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>

<HR COLOR="Black" ALIGN="CENTER" NOSHADE SIZE="1" STYLE="width: 25%; margin-top: 3pt; margin-bottom: 3pt">
<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>
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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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<DOCUMENT>
<TYPE>EX-5.1
<SEQUENCE>2
<FILENAME>ex5-1.htm
<DESCRIPTION>OPINION OF HOLLAND & KNIGHT LLP
<TEXT>
<HTML>
<HEAD>
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<!-- Field: Rule-Page --><DIV STYLE="margin-top: 12pt; margin-bottom: 3pt; width: 100%"><DIV STYLE="font-size: 1pt; border-top: Black 2pt solid; border-bottom: Black 1pt solid">&nbsp;</DIV></DIV><!-- Field: /Rule-Page -->

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><A HREF="tmp-s8_103023.htm">Tompkins Financial Corporation S-8</A></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">&nbsp;</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"><IMG SRC="ex51001.jpg" ALT=""></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; text-align: right"><B>Exhibit 5.1</B></P>

<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">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">October 31, 2023</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">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">Board of Directors</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">Tompkins Financial Corporation</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">P.O. Box 460</P>

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

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

<TABLE CELLPADDING="0" CELLSPACING="0" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0pt; width: 100%"><TR STYLE="vertical-align: top; text-align: justify">
<TD STYLE="width: 0.5in"></TD><TD STYLE="width: 0.5in; text-align: left">Re:</TD><TD STYLE="text-align: justify"><U>Registration Statement on Form S-8 of Tompkins Financial
Corporation</U></TD>
</TR></TABLE>

<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">Dear Ladies and Gentlemen:</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; text-align: justify; text-indent: 0.5in">On or about the date
hereof, Tompkins Financial Corporation, a New York corporation (the &ldquo;<U>Company</U>&rdquo;), transmitted for filing with
the Securities and Exchange Commission (the &ldquo;<U>Commission</U>&rdquo;) a Registration Statement on Form S-8 pursuant to the
Securities Act of 1933, as amended (the &ldquo;<U>Securities Act</U>&rdquo;). The Registration Statement relates to 1,000,000 shares
(the &ldquo;<U>Shares</U>&rdquo;) of the Company&rsquo;s common stock, $0.10 par value per share (&ldquo;<U>Common Stock</U>&rdquo;),
issuable under the Company&rsquo;s Tompkins Financial Corporation 2019 Equity Incentive Plan, as amended by Amendment No. 1 to
the Plan (the &ldquo;<U>Plan</U>&rdquo;). We have acted as counsel to the Company in connection with the preparation and filing
of the Registration Statement.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">In connection therewith,
we have examined and relied upon the original or a copy, certified or otherwise identified to our satisfaction, of: (i) the Company&rsquo;s
Amended and Restated Certificate of Incorporation, as amended and restated to date (the &ldquo;<U>Certificate</U>&rdquo;), and
Second Amended and Restated Bylaws, as amended to the date hereof; (ii) records of corporate proceedings (the &ldquo;<U>Corporate
Proceedings</U>&rdquo;) of the Company related to the Plan; (iii) the Registration Statement and exhibits thereto; and (iv) such
other documents, instruments and records as we have deemed necessary for the expression of the opinions contained herein.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">We have assumed the
genuineness of all signatures, the legal capacity of all natural persons, the authenticity of the documents submitted to us as
originals, the conformity with the originals of all documents submitted to us as certified, facsimile or photostatic copies and
the authenticity of the originals of all documents submitted to us as copies.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">Based upon the foregoing
examination, and subject to the assumptions, qualifications and limitations stated herein, and assuming that the consideration,
if any, required to be paid in connection with the issuance and sale of Shares under the Plan is actually received by the Company
as provided in the Plan, we are of the opinion that the Shares issued under the Plan will be duly authorized, validly issued, fully
paid and nonassessable.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">The opinion rendered
herein is limited to the New York Business Corporation Law, as amended. We express no opinion herein as to any other statutes,
rules or regulations.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">This opinion is rendered
solely in connection with the filing of the Registration Statement, is limited to the matters stated herein, and no opinions may
be implied or inferred beyond the matters expressly stated herein. This opinion may not be relied upon for any other purpose without
our prior written consent in each instance. Further, no portion of this letter may be quoted, circulated or referred to in any
other document for any other purpose without our prior written consent.</P>

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

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    <DIV STYLE="page-break-before: always; margin-top: 6pt; margin-bottom: 6pt"><P STYLE="margin: 0pt">&nbsp;</P></DIV>
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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">We hereby consent to
the filing of this opinion as Exhibit 5.1 to the Registration Statement.&nbsp; In giving such consent, we do not thereby admit
that we are in the category of persons whose consent is required under Section&nbsp;7 of the Securities Act or the rules and regulations
of the Commission promulgated thereunder.</P>

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

<TABLE CELLPADDING="0" CELLSPACING="0" STYLE="border-collapse: collapse; width: 100%; font: 10pt Times New Roman, Times, Serif">
<TR STYLE="vertical-align: bottom">
    <TD STYLE="width: 54%">&nbsp;</TD>
    <TD STYLE="width: 46%">Sincerely yours,</TD></TR>
<TR STYLE="vertical-align: bottom">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: bottom">
    <TD>&nbsp;</TD>
    <TD>/s/ Holland &amp; Knight LLP</TD></TR>
<TR STYLE="vertical-align: bottom">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: bottom">
    <TD>&nbsp;</TD>
    <TD STYLE="font-weight: bold">HOLLAND &amp; KNIGHT LLP</TD></TR>
</TABLE>


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

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<DOCUMENT>
<TYPE>EX-23.1
<SEQUENCE>3
<FILENAME>ex23-1.htm
<DESCRIPTION>CONSENT OF KPMG LLP, INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM
<TEXT>
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<BODY STYLE="font: 10pt Times New Roman, Times, Serif">

<!-- Field: Rule-Page --><DIV STYLE="margin-top: 12pt; margin-bottom: 3pt; width: 100%"><DIV STYLE="font-size: 1pt; border-top: Black 2pt solid; border-bottom: Black 1pt solid">&nbsp;</DIV></DIV><!-- Field: /Rule-Page -->

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><A HREF="tmp-s8_103023.htm">Tompkins Financial Corporation S-8</A></P>

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

<P STYLE="text-align: right; margin-top: 0; margin-bottom: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Exhibit 23.1</B></FONT></P>

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

<P STYLE="text-align: center; margin-top: 0; margin-bottom: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Consent
of Independent Registered Public Accounting Firm</B></FONT></P>

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

<P STYLE="text-align: left; margin-top: 0; margin-bottom: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">We
consent to the use of our reports dated March 1, 2023, with respect to the consolidated financial statements of Tompkins Financial Corporation,
and the effectiveness of internal control over financial reporting, incorporated herein by reference.</FONT></P>

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

<TABLE CELLPADDING="0" CELLSPACING="0" STYLE="border-collapse: collapse; font: 10pt Times New Roman, Times, Serif; width: 100%">
<TR STYLE="vertical-align: top; text-align: left">
  <TD STYLE="width: 60%">&nbsp;</TD>
  <TD STYLE="width: 40%">/s/ KPMG LLP</TD></TR>
</TABLE>

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

<P STYLE="margin: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Rochester, New York</FONT></P>

<P STYLE="margin: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">October 31, 2023</FONT></P>

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

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<DOCUMENT>
<TYPE>EX-FILING FEES
<SEQUENCE>4
<FILENAME>ex107.htm
<DESCRIPTION>CALCULATION OF FILING FEE TABLES
<TEXT>
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<BODY STYLE="font: 10pt Times New Roman, Times, Serif">
<!-- Field: Rule-Page --><DIV STYLE="margin-top: 12pt; margin-bottom: 3pt; width: 100%"><DIV STYLE="font-size: 1pt; border-top: Black 2pt solid; border-bottom: Black 1pt solid">&nbsp;</DIV></DIV><!-- Field: /Rule-Page -->

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><A HREF="tmp-s8_103023.htm">Tompkins Financial Corporation S-8</A></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; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: right"><B>Exhibit 107</B></P>

<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: 12pt 0 0px; text-align: center"><B>Calculation of Filing Fee Tables</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 12pt 0 0px; text-align: center"><B>Form S-8<BR>
(</B>Form Type)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 12pt 0 0px; text-align: center"><B>Tompkins Financial Corporation<BR>
</B>(Exact Name of Registrant as Specified in its Charter)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 12pt 0; text-align: center"><B>Table 1 -- Newly Registered Securities</B></P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%; border-collapse: collapse">
  <TR>
    <TD STYLE="width: 9%; border: Black 1pt solid; text-align: center"><B>Security Type</B></TD>
    <TD STYLE="width: 13%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center"><B>Security Class Title</B></TD>
    <TD STYLE="width: 13%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center"><B>Fee Calculation Rule</B></TD>
    <TD STYLE="width: 13%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center"><B>Amount Registered<SUP>(1)</SUP></B></TD>
    <TD STYLE="width: 12%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center"><B>Proposed Maximum Offering Price Per Unit<SUP>(3)</SUP></B></TD>
    <TD STYLE="width: 18%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center"><B>Maximum Aggregate Offering Price<SUP>(3)</SUP></B></TD>
    <TD STYLE="width: 10%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center"><B>Fee Rate</B></TD>
    <TD STYLE="width: 12%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center"><B>Amount of Registration Fee</B></TD></TR>
  <TR>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; border-left: Black 1pt solid; text-align: center">Equity</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">Common Stock, par value $0.10</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">457(h)(1) and 457(c)</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">1,000,000<SUP>(2)</SUP></TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">$49.57</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">$49,570,000.00</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">0.00014760</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">$7,316.53</TD></TR>
  <TR>
    <TD COLSPAN="4" STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; border-left: Black 1pt solid"><B>Total Offering Amounts</B></TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">&nbsp;</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">&nbsp;</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">&nbsp;</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">$7,316.53</TD></TR>
  <TR>
    <TD COLSPAN="4" STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; border-left: Black 1pt solid"><B>Total Fee Offsets<SUP>(4)</SUP></B></TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">&nbsp;</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">&nbsp;</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">&nbsp;</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">--</TD></TR>
  <TR>
    <TD COLSPAN="4" STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; border-left: Black 1pt solid"><B>Net Fee Due</B></TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">&nbsp;</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">&nbsp;</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">&nbsp;</TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; text-align: center">$7,316.53</TD></TR>
  </TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>&nbsp;</B></P>

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

<TABLE CELLPADDING="0" CELLSPACING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in">(1)</TD><TD>Pursuant to Rule 416(a), the Registration Statement also includes an indeterminate number of additional shares that may become issuable
pursuant to antidilution provisions of the 2019 Equity Incentive Plan.</TD></TR></TABLE>

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

<TABLE CELLPADDING="0" CELLSPACING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in">(2)</TD><TD>Represents 1,000,000 additional shares of common stock reserved for issuance under the Registrant&rsquo;s 2019 Equity Incentive Plan.</TD></TR></TABLE>

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

<TABLE CELLPADDING="0" CELLSPACING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in">(3)</TD><TD>In accordance with Rules 457(h) and 457(c), calculated on the basis of the average of the high and low prices of the Common Stock
on the NYSE American on October 27, 2023.</TD></TR></TABLE>

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

<TABLE CELLPADDING="0" CELLSPACING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in">(4)</TD><TD>The Registrant does not have any fee offsets.</TD></TR></TABLE>

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

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<DOCUMENT>
<TYPE>GRAPHIC
<SEQUENCE>5
<FILENAME>ex51001.jpg
<DESCRIPTION>GRAPHIC
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#7__9

end
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
