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<P STYLE="font: 11pt Times New Roman, Times, Serif; margin: 0; text-align: right"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">As
filed with the Securities and Exchange Commission on May 13, 2019</FONT></P>

<P STYLE="font: 11pt Times New Roman, Times, Serif; margin: 0; text-align: right"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">SEC
Registration No. 333-</FONT></P>

<P STYLE="font: 1pt Times New Roman, Times, Serif; margin: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></P>

<P STYLE="font: 1pt Times New Roman, Times, Serif; margin: 0"></P>

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

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

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

<P STYLE="font: 12pt 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; text-align: center"><B></B></P>

<HR ALIGN="CENTER" NOSHADE SIZE="1" STYLE="color: Black; width: 25%; margin-top: 3pt; margin-bottom: 3pt">
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>&nbsp;</B></P>

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

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

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

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

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

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

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

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

<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; text-align: center"><B>NEW YORK</B></P>

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

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

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

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

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

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

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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 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>Francis M. Fetsko</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 Operating 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>And Chief Financial Officer</B></TD>
    <TD STYLE="vertical-align: bottom">&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center"><B>Executive Vice President and General Counsel</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>Tompkins Financial Corporation</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>P.O. Box 460</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>Ithaca, New York 14851</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">&nbsp;</TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center">(Name and Address of Agent For Service)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 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: 0; text-align: center"><B>(607) 274-7685</B></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center">&nbsp;</P></TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center">(Telephone number, including area code, of agent
for service)</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">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 &#8220;large accelerated filer,&#8221; &#8220;accelerated filer,&#8221; &#8220;non-accelerated filer,&#8221; &#8220;smaller
reporting company,&#8221; and emerging growth company&#8221; in Rule 12b-2 of the Exchange Act. (Check one):</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; border-collapse: collapse">
<tr style="vertical-align: top; text-align: left;">
    <TD STYLE="width: 25%">&nbsp;</TD>
<TD STYLE="width: 20%">Large Accelerated Filer </td>
    <TD STYLE="width: 5%">&#9746;</TD>
<TD STYLE="width: 20%">Accelerated Filer </td>
    <TD STYLE="width: 5%">&#9744;</TD>
    <TD STYLE="width: 25%">&nbsp;</TD>
</tr>
<TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
<TD>Non-accelerated Filer </TD>
    <TD>&#9744;</TD>
<TD>Smaller Reporting Company </TD>
    <TD>&#9744;</TD>
    <TD>&nbsp;</TD>
</TR>
<TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
<TD>&nbsp;</TD>
    <TD></TD>
<TD>Emerging Growth Company </TD>
    <TD>&#9744;</TD>
    <TD>&nbsp;</TD>
</TR>
</TABLE>

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 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;&nbsp;&#9744;</P>

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>&nbsp;</B></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: 4%; padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; vertical-align: bottom">&nbsp;</TD>
    <TD STYLE="width: 20%; border-bottom: Black 1pt solid; padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; vertical-align: bottom">
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>&nbsp;</B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>Title of securities</B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>to be registered</B></P></TD>
    <TD STYLE="width: 18%; border-bottom: Black 1pt solid; padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; vertical-align: bottom">
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0"><B>&nbsp;</B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0"><B>Amount to be</B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0"><B>registered <SUP>(1)</SUP></B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0"><SUP></SUP></P></TD>
    <TD STYLE="width: 17%; border-bottom: Black 1pt solid; padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; vertical-align: bottom">
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>Proposed maximum</B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>offering price per</B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>share <SUP>(2)</SUP></B></P></TD>
    <TD STYLE="width: 22%; border-bottom: Black 1pt solid; padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; vertical-align: bottom">
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>Proposed maximum</B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>aggregate </B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>offering price</B> <SUP>(2)</SUP></P></TD>
    <TD STYLE="width: 19%; border-bottom: Black 1pt solid; padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; vertical-align: bottom">
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>Amount of </B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>registration</B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>fee</B></P>
        <P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0"><B></B></P></TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; white-space: nowrap">&nbsp;</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; white-space: nowrap">
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center">Common Stock, $.10 par value</P></TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; white-space: nowrap">1,275,000</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; white-space: nowrap">$78.59</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; white-space: nowrap">$100,202,250</TD>
    <TD STYLE="padding-right: 5.4pt; padding-left: 5.4pt; text-align: center; white-space: nowrap">$12,145</TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>&nbsp;</B></P>

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

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

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0"></TD><TD STYLE="width: 0.5in"><SUP>(2)</SUP></TD><TD>In accordance with Rules 457(h)(1) and 457(c), calculated on the basis of the high and low prices of the Common Stock on the
NYSE-American on May 9, 2019.</TD></TR></TABLE>

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


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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 12pt 0 0; text-align: center"><B>INFORMATION REQUIRED IN THE SECTION
10(a) PROSPECTUS</B></P>

<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; text-indent: 0.5in">The documents containing the information specified
in Part I of Form S-8 will be sent or given to employees as specified by Rule 428(b)(1) under the Securities Act of 1933, as amended
(the &#8220;Securities Act&#8221;). Such documents need not be filed with the Securities and Exchange Commission (the &#8220;Commission&#8221;)
either as part of this Registration Statement or as prospectuses or prospectus supplements pursuant to Rule 424 under the Securities
Act. These documents and the documents incorporated by reference in this Registration Statement pursuant to Item 3 of Part II of
this form, taken together, constitute a prospectus that meets the requirements of Section 10(a) of the Securities Act.</P>

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

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

<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; text-align: center"><B>INFORMATION REQUIRED IN THE REGISTRATION
STATEMENT</B></P>

<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"><B>Item 3. Incorporation of Documents by Reference.</B></P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">The following documents are incorporated by reference in this Registration
Statement:</P>

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

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

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0">                                                                                                                                      <TR STYLE="vertical-align: top">
<TD>&nbsp;</TD><TD>(a)</TD><TD>The Registrant&#8217;s
Annual Report on Form 10-K for the fiscal year ended December 31, 2018.</TD></TR>
<TR STYLE="vertical-align: top">
<TD>&nbsp;</TD><TD>&nbsp;</TD><TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in"></TD><TD STYLE="width: 0.5in">(b)</TD><TD>All other reports filed pursuant to Section 13(a) or 15(d) of the Exchange Act since the end of the fiscal year covered by
the Registrant&#8217;s Annual Report referred to in (a) above.</TD></TR></TABLE>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0 0 0 1in; text-indent: -0.5in">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in"></TD><TD STYLE="width: 0.5in">(c)</TD><TD>The description of the Common Stock of the Registrant contained in the Registrant&#8217;s Registration Statement on Form 8-A
(No. 1-12709) filed with the Commission on January 30, 1997, including any amendment(s) or report(s) filed for the purpose of updating
such description.</TD></TR></TABLE>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0 0 0 1in; text-indent: -0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in">All documents subsequently filed by the Registrant
pursuant to Sections 13(a), 13(c), 14 and 15(d) of the Securities Exchange Act of 1934 (the &#8220;Exchange Act&#8221;), prior
to the filing of a post-effective amendment to this Registration Statement which indicates that all of the shares of common stock
offered have been sold or which 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. Any statement contained in a
document incorporated or deemed to be incorporated by reference herein shall be deemed to be modified or superseded for purposes
of this Registration Statement to the extent that a statement contained herein or in any other subsequently filed document which
also is or is deemed to be incorporated by reference herein modifies or supersedes such statement. Any such statement so modified
or superseded shall not be deemed, except as so modified or superseded, to constitute a part of this Registration Statement.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><B>Item 4. Description of Securities.</B></P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in">Not applicable.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><B>Item 5. Interests of Named Experts and Counsel.</B></P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in">Not applicable.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><B>Item 6. Indemnification of Directors and Officers.</B></P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in">Sections 721-725 of the New York Business
Corporation Law generally provide for or permit a New York corporation to indemnify any person who is, or is threatened to
be, made party to any action or proceeding (other than one by or in the right of the corporation to procure a judgment in its
favor), whether civil or criminal, by reason of the fact that such person (or such person&#8217;s testator or intestate), was
an officer or director of such corporation, or served at the request of such corporation as a director, officer, employee,
agent, or in any other capacity, of another corporation or enterprise. The indemnity may include judgments, fines, amounts
paid in settlement and reasonable expenses, including attorneys&#8217; fees actually and necessarily incurred by such person
as a result of such action or proceeding, or any appeal therein, provided that such officer or director acted in good faith,
for a purpose that he or she reasonably believed to be in or, in the case of service for another corporation or enterprise,
not opposed to, the best interests of the corporation and, for criminal actions or proceedings, in addition, had no
reasonable cause to believe his or her conduct was unlawful. A New York corporation may indemnify any officer or director
against amounts paid in settlement and reasonable expenses, including attorneys&#8217; fees, actually and necessarily
incurred by him or her in connection with the defense or settlement of an action by or in the right of the corporation under the same conditions, except that
no indemnification is permitted in respect of (1) a threatened action, or a pending action which is settled or otherwise disposed
of, or (2) any claim, issue or matter as to which such person shall have been adjudged to be liable to the corporation, unless
and only to the extent judicially approved. Where an officer or director is successful on the merits or otherwise in the defense
of an action referred to above, the corporation must indemnify him or her against the expenses which such officer or director actually
and reasonably incurred. Article VIII of the Registrant&#8217;s By-Laws provides for indemnification for the officers and directors
of the Registrant to the fullest extent permitted by applicable law.</P>

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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in">In accordance with Section 402(b) of the New
York Business Corporation Law, the Registrant&#8217;s Certificate of Incorporation contains a provision to limit the personal liability
of the directors of the Registrant to the fullest extent permitted under the Business Corporation Law; provided, however, that
there shall be no limitation of a director&#8217;s liability for acts or omissions committed in bad faith, or that involved intentional
misconduct or a knowing violation of law, or from which a director personally gained a financial profit or other advantage to which
he or she was not legally entitled. The effect of this provision is to eliminate the personal liability of directors to the Registrant
and its shareholders for monetary damages for actions involving a breach of their fiduciary duty of care, including any such actions
involving gross negligence.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><B>Item 7. Exemption From Registration Claimed.</B></P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in">Not applicable.</P>

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

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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in">The following exhibits are filed with this Registration
Statement:</P>

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

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

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

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in"></TD><TD STYLE="width: 0.5in">5</TD><TD>Opinion of Harris Beach PLLC</TD></TR></TABLE>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0 0 0 1in; text-indent: -0.5in">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in"></TD><TD STYLE="width: 0.5in">23.1</TD><TD>Consent of KPMG LLP, Independent Registered Public Accounting Firm</TD></TR></TABLE>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0 0 0 1in; text-indent: -0.5in">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in"></TD><TD STYLE="width: 0.5in">23.2</TD><TD>Consent of Harris Beach PLLC (included in Exhibit 5)</TD></TR></TABLE>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0 0 0 1in; text-indent: -0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0 0 0 0.5in"></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"></TD><TD STYLE="width: 0.5in">24</TD><TD>Power of Attorney
(included at pages II-4 and II-5)</TD></TR>
</TABLE>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0 0 0 1in; text-indent: -0.5in">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in"></TD><TD STYLE="width: 0.5in"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000138713119002241/tmp-def14a_050719.htm">99</A></FONT></TD><TD><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">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.</FONT></TD></TR></TABLE>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><B>Item 9. Undertakings.</B></P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">(a)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The Registrant hereby
undertakes:</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in">(1)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;To
file, during any period in which offers or sales are being made, a post-effective amendment to this registration statement:</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 1in">(i)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;To
include any propectus required by Section 10(a)(3) of the Securities Act;</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 1in">(ii)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;To
reflect in the prospectus any facts or events arising after the effective date of the registration statement (or the most recent
post-effective amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set
forth in the registration statement. Notwithstanding the foregoing, any increase or decrease in volume of securities offered (if
the total dollar value of securities offered would not exceed that which was registered) and any deviation from the low or high
end of the estimated maximum offering range may be reflected in the form of prospectus filed with the Commission pursuant to Rule
424(b) if, in the aggregate, the changes in volume and price represent no more than 20% change in the maximum aggregate offering
price set forth in the &#8220;Calculation of Registration Fee&#8221; table in the effective registration statement.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 1in">(iii)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;To
include any material information with respect to the plan of distribution not previously disclosed in the registration statement
or any material change to such information in the registration statement; <I>provided, however, </I>that paragraphs (a)(1)(i) and
(a)(1)(ii) do not apply if the information required to be included in a post-effective amendment by those paragraphs is contained
in periodic reports filed with or furnished to the Commission by the Registrant pursuant to Section 13 or Section 15(d) of the
Exchange Act that are incorporated by reference in this registration statement.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in">(2)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;That,
for the purpose of determining any liability under the Securities Act, each such post-effective amendment shall be deemed to be
a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall
be deemed to be the initial <I>bona fide </I>offering thereof.</P>

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

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


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


<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in">(3)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;To
remove from registration by means of a post-effective amendment any of the securities being registered which remain unsold at the
termination of the offering.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">(b)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The undersigned Registrant
hereby undertakes that, for purposes of determining any liability under the Securities Act, each filing of the Registrant&#8217;s
annual report pursuant to Section 13(a) or Section 15(d) of the Exchange Act that is incorporated by reference in this Registration
Statement shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such
securities at that time shall be deemed to be the initial <I>bona fide</I> offering thereof.</P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">(c)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Insofar as indemnification
for liabilities arising under the Securities Act of 1933 may be permitted to directors, officers and controlling persons of the
Registrant pursuant to the foregoing provisions, or otherwise, the Registrant has been advised that in the opinion of the Securities
and Exchange Commission such indemnification is against public policy as expressed in the Act and is, therefore, unenforceable.
In the event that a claim for indemnification against such liabilities (other than the payment by the Registrant of expenses incurred
or paid by a director, officer or controlling person of the Registrant in the successful defense of any action, suit or proceeding)
is asserted by such director, officer or controlling person in connection with the securities being registered, the Registrant
will, unless in the opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate
jurisdiction the question whether such indemnification by it is against public policy as expressed in the Act and will be governed
by the final adjudication of such issue.</P>

<P STYLE="font: 2pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

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


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<P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>


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

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

<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; 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 13<SUP>th</SUP> day of May, 2019.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 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 STYLE="padding-bottom: 8pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="padding-bottom: 8pt">TOMPKINS FINANCIAL CORPORATION</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="width: 60%; padding-bottom: 8pt">&nbsp;</TD>
    <TD STYLE="width: 6%; padding-bottom: 8pt">&nbsp;</TD>
    <TD STYLE="width: 34%; padding-bottom: 8pt">&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: 8pt Times New Roman, Times, Serif; margin: 0 0 8pt"></P>

<P STYLE="font: 2pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0"></P>

<P STYLE="font: 8pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B><A NAME="a_001"></A>POWER OF ATTORNEY</B></P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 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 Francis M. Fetsko
and each of them, as his true and lawful attorneys-in-fact and agents, each with full power of substitution, for him, and in his
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 he 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: 0">&nbsp;</P>

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"></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: 23%; text-align: center"><B>Name</B></TD>
    <TD STYLE="width: 9%">&nbsp;</TD>
    <TD STYLE="width: 50%"><B>Capacity</B></TD>
    <TD STYLE="width: 18%"><B>Date</B></TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="text-align: center">&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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>Chairman of the Board </TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Thomas R. Rochon</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></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Stephen S. Romaine&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD ROWSPAN="2">President and Chief Executive Officer, Director<BR>
(Principal Executive Officer) </TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Stephen S. Romaine</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></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ James W. Fulmer&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>Vice Chairman, Director</TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>James W. Fulmer</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></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Francis M. Fetsko&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD ROWSPAN="3"><P STYLE="margin-top: 0; margin-bottom: 0">Executive Vice President, Chief Financial Officer</P>
                    <P STYLE="margin-top: 0; margin-bottom: 0">Chief Operating Officer (Principal Financial Officer and <BR> Principal Accounting Officer)</P></TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Francis M. Fetsko</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <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></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ John E. Alexander&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>John E. Alexander</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></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Paul J. Battaglia&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Paul J. Battaglia</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></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Daniel J. Fessenden&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Daniel J. Fessenden</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></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

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


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<P STYLE="font: 10pt Times New Roman, Times, Serif; 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: 23%">&nbsp;</TD>
    <TD STYLE="width: 9%">&nbsp;</TD>
    <TD STYLE="width: 50%">&nbsp;</TD>
    <TD STYLE="width: 18%">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Patricia A. Johnson&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Patricia A. Johnson</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></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Frank C. Milewski</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Frank C. Milewski</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></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Michael H. Spain&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Michael H. Spain</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></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>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Alfred J. Weber</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></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="border-bottom: Black 1pt solid">/s/ Craig Yunker&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&#9;</TD>
    <TD>&nbsp;</TD>
    <TD>Director</TD>
    <TD>April 25, 2019</TD></TR>
<TR STYLE="vertical-align: top">
    <TD>Craig Yunker</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
</TABLE>
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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>EXHIBIT INDEX</B></P>

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

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-bottom: 0"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0"></TD><TD STYLE="width: 0.5in"><A HREF="ex-5.htm">5</A></TD><TD>Opinion of Harris Beach PLLC</TD></TR></TABLE>

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<TD STYLE="width: 0"></TD><TD STYLE="width: 0.5in"><A HREF="ex23-1.htm">23.1</A></TD><TD>Consent of KPMG LLP, Independent Registered Public Accounting Firm</TD></TR></TABLE>

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<TD STYLE="width: 0"></TD><TD STYLE="width: 0.5in"><A HREF="ex-5.htm">23.2</A></TD><TD>Consent of Harris Beach PLLC (included in Exhibit 5)</TD></TR></TABLE>

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<TD STYLE="width: 0"></TD><TD STYLE="width: 0.5in"><A HREF="#a_001">24</A></TD><TD>Power of Attorney (included at pages II-4 and II-5)</TD></TR></TABLE>

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<TD STYLE="width: 0"></TD><TD STYLE="width: 0.5in"><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000138713119002241/tmp-def14a_050719.htm">99</A></TD><TD>Tompkins Financial Corporation 2019 Equity Incentive Plan, incorporated herein by reference to Appendix A of the Company&#8217;s
DEF 14A filed with the commission on March 29, 2019</TD></TR></TABLE>

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[{"type": "S-8", "sequence": "1", "filename": "tmp-s8_051319.htm", "description": "INITIAL REGISTRATION STATEMENT FOR SECURITIES TO BE OFFER TO EMPLOYEES", "secsgml_size_bytes": 51876}]
{"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": "333-231413", "film-number": "19818189"}, "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 May 13, 2019
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)
Francis M. Fetsko
with a copy to:
Executive Vice President, Chief Operating Officer
Alyssa H. Fontaine
And Chief Financial Officer
Executive Vice President and General Counsel
Tompkins Financial Corporation
Tompkins Financial Corporation
P.O. Box 460
P.O. Box 460
Ithaca, New York 14851
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.  ☐
CALCULATION OF REGISTRATION FEE
Title of securities
to be registered
Amount to be
registered
(1)
Proposed maximum
offering price per
share
(2)
Proposed maximum
aggregate
offering price
(2)
Amount of
registration
fee
Common Stock, $.10 par value
1,275,000
$78.59
$100,202,250
$12,145
(1)
The Registration Statement also includes an indeterminate number of additional shares that may become issuable pursuant
                                                                      to antidilution provisions of the 2019 Equity Plan.
(2)
In accordance with Rules 457(h)(1) and 457(c), calculated on the basis of the high and low prices of the Common Stock on the
NYSE-American on May 9, 2019.
PART I
INFORMATION REQUIRED IN THE SECTION
10(a) PROSPECTUS
The documents containing the information specified
in Part I of Form S-8 will be sent or given to employees as specified by Rule 428(b)(1) under the Securities Act of 1933, as amended
(the "Securities Act"). Such documents need not be filed with the Securities and Exchange Commission (the "Commission")
either as part of this Registration Statement or as prospectuses or prospectus supplements pursuant to Rule 424 under the Securities
Act. These documents and the documents incorporated by reference in this Registration Statement pursuant to Item 3 of Part II of
this form, taken together, constitute a prospectus that meets the requirements of Section 10(a) of the Securities Act.
PART II
INFORMATION REQUIRED IN THE REGISTRATION
STATEMENT
Item 3. Incorporation of Documents by Reference.
The following documents are incorporated by reference in this Registration
Statement:
(a)
The Registrant's
Annual Report on Form 10-K for the fiscal year ended December 31, 2018.
(b)
All other reports filed pursuant to Section 13(a) or 15(d) of the Exchange Act since the end of the fiscal year covered by
the Registrant's Annual Report referred to in (a) above.
(c)
The description of the Common Stock of the Registrant contained in the Registrant's Registration Statement on Form 8-A
(No. 1-12709) filed with the Commission on January 30, 1997, including any amendment(s) or report(s) filed for the purpose of updating
such description.
All documents subsequently filed by the Registrant
pursuant to Sections 13(a), 13(c), 14 and 15(d) of the Securities Exchange Act of 1934 (the "Exchange Act"), prior
to the filing of a post-effective amendment to this Registration Statement which indicates that all of the shares of common stock
offered have been sold or which 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. Any statement contained in a
document incorporated or deemed to be incorporated by reference herein shall be deemed to be modified or superseded for purposes
of this Registration Statement to the extent that a statement contained herein or in any other subsequently filed document which
also is or is deemed to be incorporated by reference herein modifies or supersedes such statement. Any such statement so modified
or superseded shall not be deemed, except as so modified or superseded, to constitute a part of this Registration Statement.
Item 4. Description of Securities.
Not applicable.
Item 5. Interests of Named Experts and Counsel.
Not applicable.
.
Item 6. Indemnification of Directors and Officers.
Sections 721-725 of the New York Business
Corporation Law generally provide for or permit a New York corporation to indemnify any person who is, or is threatened to
be, made party to any action or proceeding (other than one by or in the right of the corporation to procure a judgment in its
favor), whether civil or criminal, by reason of the fact that such person (or such person's testator or intestate), was
an officer or director of such corporation, or served at the request of such corporation as a director, officer, employee,
agent, or in any other capacity, of another corporation or enterprise. The indemnity may include judgments, fines, amounts
paid in settlement and reasonable expenses, including attorneys' fees actually and necessarily incurred by such person
as a result of such action or proceeding, or any appeal therein, provided that such officer or director acted in good faith,
for a purpose that he or she reasonably believed to be in or, in the case of service for another corporation or enterprise,
not opposed to, the best interests of the corporation and, for criminal actions or proceedings, in addition, had no
reasonable cause to believe his or her conduct was unlawful. A New York corporation may indemnify any officer or director
against amounts paid in settlement and reasonable expenses, including attorneys' fees, actually and necessarily
incurred by him or her in connection with the defense or settlement of an action by or in the right of the corporation under the same conditions, except that
no indemnification is permitted in respect of (1) a threatened action, or a pending action which is settled or otherwise disposed
of, or (2) any claim, issue or matter as to which such person shall have been adjudged to be liable to the corporation, unless
and only to the extent judicially approved. Where an officer or director is successful on the merits or otherwise in the defense
of an action referred to above, the corporation must indemnify him or her against the expenses which such officer or director actually
and reasonably incurred. Article VIII of the Registrant's By-Laws provides for indemnification for the officers and directors
of the Registrant to the fullest extent permitted by applicable law.
II-
1
In accordance with Section 402(b) of the New
York Business Corporation Law, the Registrant's Certificate of Incorporation contains a provision to limit the personal liability
of the directors of the Registrant to the fullest extent permitted under the Business Corporation Law; provided, however, that
there shall be no limitation of a director's liability for acts or omissions committed in bad faith, or that involved intentional
misconduct or a knowing violation of law, or from which a director personally gained a financial profit or other advantage to which
he or she was not legally entitled. The effect of this provision is to eliminate the personal liability of directors to the Registrant
and its shareholders for monetary damages for actions involving a breach of their fiduciary duty of care, including any such actions
involving gross negligence.
Item 7. Exemption From Registration Claimed.
Not applicable.
Item 8. Exhibits.
The following exhibits are filed with this Registration
Statement:
EXHIBIT INDEX
5
Opinion of Harris Beach PLLC
23.1
Consent of KPMG LLP, Independent Registered Public Accounting Firm
23.2
Consent of Harris Beach PLLC (included in Exhibit 5)
24
Power of Attorney
(included at pages II-4 and II-5)
99
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.
Item 9. Undertakings.
(a)       The Registrant hereby
undertakes:
(1)       To
file, during any period in which offers or sales are being made, a post-effective amendment to this registration statement:
(i)       To
include any propectus required by Section 10(a)(3) of the Securities Act;
(ii)       To
reflect in the prospectus any facts or events arising after the effective date of the registration statement (or the most recent
post-effective amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set
forth in the registration statement. Notwithstanding the foregoing, any increase or decrease in volume of securities offered (if
the total dollar value of securities offered would not exceed that which was registered) and any deviation from the low or high
end of the estimated maximum offering range may be reflected in the form of prospectus filed with the Commission pursuant to Rule
424(b) if, in the aggregate, the changes in volume and price represent no more than 20% change in the maximum aggregate offering
price set forth in the "Calculation of Registration Fee" table in the effective registration statement.
(iii)       To
include any material information with respect to the plan of distribution not previously disclosed in the registration statement
or any material change to such information in the registration statement;
provided, however,
that paragraphs (a)(1)(i) and
(a)(1)(ii) do not apply if the information required to be included in a post-effective amendment by those paragraphs is contained
in periodic reports filed with or furnished to the Commission by the Registrant pursuant to Section 13 or Section 15(d) of the
Exchange Act that are incorporated by reference in this registration statement.
(2)       That,
for the purpose of determining any liability under the Securities Act, each such post-effective amendment shall be deemed to be
a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall
be deemed to be the initial
bona fide
offering thereof.
II-
2
(3)       To
remove from registration by means of a post-effective amendment any of the securities being registered which remain unsold at the
termination of the offering.
(b)       The undersigned Registrant
hereby undertakes that, for purposes of determining any liability under the Securities Act, each filing of the Registrant's
annual report pursuant to Section 13(a) or Section 15(d) of the Exchange Act that is incorporated by reference in this Registration
Statement shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such
securities at that time shall be deemed to be the initial
bona fide
offering thereof.
(c)       Insofar as indemnification
for liabilities arising under the Securities Act of 1933 may be permitted to directors, officers and controlling persons of the
Registrant pursuant to the foregoing provisions, or otherwise, the Registrant has been advised that in the opinion of the Securities
and Exchange Commission such indemnification is against public policy as expressed in the Act and is, therefore, unenforceable.
In the event that a claim for indemnification against such liabilities (other than the payment by the Registrant of expenses incurred
or paid by a director, officer or controlling person of the Registrant in the successful defense of any action, suit or proceeding)
is asserted by such director, officer or controlling person in connection with the securities being registered, the Registrant
will, unless in the opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate
jurisdiction the question whether such indemnification by it is against public policy as expressed in the Act and will be governed
by the final adjudication of such issue.
II-
3
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 13
th
day of May, 2019.
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 Francis M. Fetsko
and each of them, as his true and lawful attorneys-in-fact and agents, each with full power of substitution, for him, and in his
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 he 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/ Thomas R. Rochon
Chairman of the Board
April 25, 2019
Thomas R. Rochon
/s/ Stephen S. Romaine
President and Chief Executive Officer, Director
(Principal Executive Officer)
April 25, 2019
Stephen S. Romaine
/s/ James W. Fulmer
Vice Chairman, Director
April 25, 2019
James W. Fulmer
/s/ Francis M. Fetsko
Executive Vice President, Chief Financial Officer
Chief Operating Officer (Principal Financial Officer and
Principal Accounting Officer)
April 25, 2019
Francis M. Fetsko
/s/ John E. Alexander
Director
April 25, 2019
John E. Alexander
/s/ Paul J. Battaglia
Director
April 25, 2019
Paul J. Battaglia
/s/ Daniel J. Fessenden
Director
April 25, 2019
Daniel J. Fessenden
II-
4
/s/ Patricia A. Johnson
Director
April 25, 2019
Patricia A. Johnson
/s/ Frank C. Milewski
Director
April 25, 2019
Frank C. Milewski
/s/ Michael H. Spain
Director
April 25, 2019
Michael H. Spain
/s/ Alfred J. Weber
Director
April 25, 2019
Alfred J. Weber
/s/ Craig Yunker
Director
April 25, 2019
Craig Yunker
II-
5
EXHIBIT INDEX
5
Opinion of Harris Beach PLLC
23.1
Consent of KPMG LLP, Independent Registered Public Accounting Firm
23.2
Consent of Harris Beach PLLC (included in Exhibit 5)
24
Power of Attorney (included at pages II-4 and II-5)
99
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
II-
6