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<!-- Field: Rule-Page --><DIV ALIGN="LEFT" STYLE="margin: 0"><DIV STYLE="font-size: 1pt; border-top: Black 2pt solid; border-bottom: Black 1pt solid; width: 100%">&nbsp;</DIV></DIV><!-- Field: /Rule-Page -->

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

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    <TD STYLE="width: 87%; text-align: right; padding-right: 0.1in">As
filed with the Securities and Exchange Commission on</TD>
    <TD STYLE="width: 13%; border-bottom: Black 1pt solid">February 1, 2019</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
    <TD STYLE="text-align: right; padding-right: 0.1in">SEC
Registration No. </TD>
    <TD STYLE="border-bottom: Black 1pt solid">&nbsp;</TD></TR>
</TABLE>

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

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

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

<P STYLE="font: 12pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 12pt"><B>SECURITIES
AND EXCHANGE COMMISSION</B></FONT></P>

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

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

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

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

<P STYLE="font: 11pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 11pt"><B>FORM
S-8</B></FONT></P>

<P STYLE="font: 11pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 11pt"><B>&nbsp;</B></FONT></P>

<P STYLE="font: 11pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 11pt"><B>REGISTRATION
STATEMENT</B></FONT></P>

<P STYLE="font: 11pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 11pt"><B>UNDER</B></FONT></P>

<P STYLE="font: 11pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 11pt"><B>THE
SECURITIES ACT OF 1933</B></FONT></P>

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

<P STYLE="font: 18pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 18pt"><B>TOMPKINS
FINANCIAL CORPORATION</B></FONT></P>

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

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

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

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

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

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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>118
E. Seneca St.</B></FONT></P>

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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0 40.1pt 0 34.55pt; text-align: center; background-color: white"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>TOMPKINS
FINANCIAL CORPORATION EMPLOYEE STOCK OWNERSHIP PLAN [ESOP]</B></FONT></P>

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

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; border-collapse: collapse">
<TR STYLE="vertical-align: bottom; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="width: 10%">&nbsp;</TD>
    <TD STYLE="width: 39%; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></TD>
    <TD STYLE="width: 2%; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></TD>
    <TD STYLE="width: 39%; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></TD>
    <TD STYLE="width: 10%">&nbsp;</TD></TR>
<TR STYLE="font: 10pt Times New Roman, Times, Serif">
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Francis
    M. Fetsko</B></FONT></TD>
    <TD STYLE="vertical-align: bottom; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>&nbsp;with
    a copy to:</B></FONT></TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="font: 10pt Times New Roman, Times, Serif">
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Executive
    Vice President, Chief Operating Officer</B></FONT></TD>
    <TD STYLE="vertical-align: bottom; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></TD>
    <TD STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Alyssa
H. Fontaine, Esq.&nbsp;</B></FONT></P></TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="font: 10pt Times New Roman, Times, Serif">
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>And
    Chief Financial Officer</B></FONT></TD>
    <TD STYLE="vertical-align: bottom; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>EVP
    &amp; General Counsel</B></FONT></TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="font: 10pt Times New Roman, Times, Serif">
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif">&nbsp;</TD>
    <TD STYLE="vertical-align: bottom; font: 10pt Times New Roman, Times, Serif">&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif">&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="font: 10pt Times New Roman, Times, Serif">
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Tompkins
    Financial Corporation</B></FONT></TD>
    <TD STYLE="vertical-align: bottom; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Tompkins
    Financial Corporation</B></FONT></TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="font: 10pt Times New Roman, Times, Serif">
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>P.O.
    Box 460</B></FONT></TD>
    <TD STYLE="vertical-align: bottom; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>P.O.
    Box 460</B></FONT></TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="font: 10pt Times New Roman, Times, Serif">
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Ithaca,
    New York 14851</B></FONT></TD>
    <TD STYLE="vertical-align: bottom; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></TD>
    <TD STYLE="vertical-align: top; text-align: center; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Ithaca,
    New York, 14851</B></FONT></TD>
    <TD>&nbsp;</TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">(Name
and Address of Agent For Service)</FONT></P>

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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">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;smaller reporting company&rdquo;, and &ldquo;emerging growth company&rdquo; in Rule 12b-2 of the Exchange Act. (Check one):</FONT></P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><FONT STYLE="font: 10pt Times New Roman, Times, Serif"></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: 15%">&nbsp;</TD>
    <TD STYLE="width: 20%">Large
accelerated filer</TD>
    <TD STYLE="width: 5%; text-align: center; vertical-align: top">&#9746;&nbsp;</TD>
    <TD STYLE="width: 15%">&nbsp;</TD>
    <TD STYLE="width: 20%">Accelerated filer</TD>
    <TD STYLE="width: 5%; text-align: center; vertical-align: top">&#9744;</TD>
    <TD STYLE="width: 20%">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD>Non-accelerated
filer</TD>
    <TD STYLE="text-align: center; vertical-align: top">&#9744;&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>Smaller reporting company</TD>
    <TD STYLE="text-align: center; vertical-align: top">&#9744;</TD>
    <TD>&nbsp;</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD STYLE="text-align: center; vertical-align: top">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD STYLE="white-space: nowrap">Emerging
Growth Company</TD>
    <TD STYLE="text-align: center; vertical-align: top">&#9744;</TD>
    <TD>&nbsp;</TD></TR>
</TABLE>

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

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

<P STYLE="font: 10pt 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: 10pt Times New Roman, Times, Serif; margin: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt; color: #211D1E">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.
</FONT><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&#9744;</FONT></P>

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

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


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

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

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

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; border-collapse: collapse">
<TR STYLE="vertical-align: top; font: bold 10pt Times New Roman, Times, Serif; color: Black">
    <TD STYLE="width: 5%; border: Black 1pt solid; font: bold 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: bottom; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>&nbsp;</B></FONT></TD>
    <TD STYLE="width: 19%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; font: bold 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: bottom; color: Black"><P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>&nbsp;</B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Title
        of securities</B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>to
        be registered</B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"></P></TD>
    <TD STYLE="width: 19%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; font: bold 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: bottom; color: Black"><P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>&nbsp;</B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Amount
        to be</B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>registered
        <SUP>(1)&nbsp;</SUP></B></FONT></P></TD>
    <TD STYLE="width: 19%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; font: bold 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: bottom; color: Black"><P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Proposed
                                         maximum</B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>offering
        price per</B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>share
        <SUP>(2)</SUP></B></FONT></P></TD>
    <TD STYLE="width: 19%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; font: bold 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: bottom; color: Black"><P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Proposed
                                         maximum</B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>aggregate
        </B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>offering
        price <SUP>(2)</SUP></B></FONT></P></TD>
    <TD STYLE="width: 19%; border-top: Black 1pt solid; border-right: Black 1pt solid; border-bottom: Black 1pt solid; font: bold 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: bottom; color: Black"><P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Amount
                                         of </B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>registration</B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>fee</B></FONT></P>
        <P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0; color: Black"></P></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; border-left: Black 1pt solid; font: 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: top"><FONT STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</FONT></TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; font: 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Common
Stock, $0.10 par value</FONT></P></TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; font: 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: top"><FONT STYLE="font: 10pt Times New Roman, Times, Serif">125,000</FONT></TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; font: 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: top"><FONT STYLE="font: 10pt Times New Roman, Times, Serif">$73.86</FONT></TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; font: 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: top"><FONT STYLE="font: 10pt Times New Roman, Times, Serif">$9,232,500</FONT></TD>
    <TD STYLE="border-right: Black 1pt solid; border-bottom: Black 1pt solid; font: 10pt Times New Roman, Times, Serif; padding: 5.4pt; text-align: center; vertical-align: top"><FONT STYLE="font: 10pt Times New Roman, Times, Serif">$1,118.98</FONT></TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0 0 0 0.5in; text-indent: -0.5in"><FONT STYLE="font: 10pt Times New Roman, Times, Serif"><SUP>&nbsp;</SUP></FONT></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; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="width: 0.5in; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font: 10pt Times New Roman, Times, Serif"><SUP>(1)</SUP></FONT></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font: 10pt Times New Roman, Times, Serif">The
                                         Registration Statement also includes an indeterminate number of additional shares that
                                         may become issuable pursuant to share splits, share dividends, antidilution provisions
                                         and other adjustments to the extent contemplated by the Tompkins Financial Corporation
                                         Employee Stock Ownership Plan (the &ldquo;ESOP&rdquo;).</FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font: 10pt Times New Roman, Times, Serif"><SUP>(2)</SUP></FONT></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font: 10pt Times New Roman, Times, Serif">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 January 28, 2019.</FONT></TD></TR></TABLE>

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

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

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

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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in; text-align: left"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Pursuant
to General Instruction E of Form S-8, this Registration Statement on Form S-8 (this &ldquo;Registration Statement&rdquo;), which
incorporates by reference the contents of the Registrant&rsquo;s previous Registration Statements on Form S-8 (No. 333-163977),
filed with the Securities and Exchange Commission on December 23, 2009; (No. 333-184582), filed with the Securities and Exchange
Commission on October 24, 2012; (No. 333-206043), filed with the Securities and Exchange Commission on August 3, 2015 (together,
the &ldquo;Prior Registration Statements&rdquo;), is being filed by the Registrant solely to register an additional 125,000 shares
for issuance under the Tompkins Financial Corporation Employee Stock Ownership Plan [ESOP]. The Prior Registration Statements
relate to the same class of securities and the same plan. Accordingly, this Registration Statement consists only of those items
required by General Instruction E to Form S-8.</FONT></P>

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

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

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

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

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

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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0 0 -11pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Item
8.</B></FONT></P>

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

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

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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0.5in"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;</FONT></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; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="width: 0.5in; font: 10pt Times New Roman, Times, Serif"></TD><TD STYLE="width: 0.5in; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">5</FONT></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Opinion
                                         of Harris Beach PLLC</FONT></TD></TR>                                                                              <TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>

<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif"></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">23.1</FONT></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Consent
                                         of KPMG LLP</FONT></TD></TR>                                                                     <TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>

<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif"></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">23.2</FONT></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Consent
                                         of Harris Beach PLLC (included in Exhibit 5)</FONT></TD></TR>                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                          <TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">24</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">Power
of Attorney (included at Pages II-2 and II-3)</TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">99</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">Tompkins
                                         Financial Corporation Employee Stock Ownership Plan (incorporated by reference to Exhibit
                                         99 to the Registrant&rsquo;s Registration Statement on Form S-8 (SEC Registration No.
                                         333-163977) filed on December 23, 2009).</TD></TR>
</TABLE>

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

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

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

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

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: left"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">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 24<SUP>th</SUP> day
of January, 2019.</FONT></P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><FONT STYLE="font: 10pt Times New Roman, Times, Serif"></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>&nbsp;</TD>
    <TD COLSPAN="3">TOMPKINS
FINANCIAL CORPORATION</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD COLSPAN="3">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
    <TD STYLE="width: 50%">&nbsp;</TD>
    <TD STYLE="width: 4%">By:</TD>
    <TD STYLE="width: 31%"><U>/s/ Stephen S. Romaine</U></TD>
    <TD STYLE="width: 15%">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD COLSPAN="2">Stephen
S. Romaine</TD></TR>
<TR STYLE="vertical-align: top; text-align: left">
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD COLSPAN="2">Chief
Executive Officer</TD></TR>
</TABLE>

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

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

<P STYLE="font: 10pt 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: 10pt Times New Roman, Times, Serif; margin: 0; text-align: left"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">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.</FONT></P>

<P STYLE="font: 10pt 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: 10pt Times New Roman, Times, Serif; margin-top: 0; margin-right: 0; margin-bottom: 0; text-align: left"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Pursuant
to the requirements of the Securities 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:</FONT></P>

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

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="width: 100%; font: 10pt Times New Roman, Times, Serif; border-collapse: collapse">
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="width: 25%; padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Name</B></FONT></TD>
    <TD STYLE="width: 50%; padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Capacity</B></FONT></TD>
    <TD STYLE="width: 25%; padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Date</B></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/ Thomas R. Rochon</U></FONT><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Thomas
        R. Rochon</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Chairman
    of the Board, Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;<U>/S/
Stephen S. Romaine</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Stephen
        S. Romaine</FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"></FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">President
    and Chief Executive Officer, Director<BR>
    (Principal Executive Officer)</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        James W. Fulmer</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">James
        W. Fulmer</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Vice
    Chairman, Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        Francis M. Fetsko</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Francis
        M. Fetsko</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Executive
    Vice President, Chief Financial Officer, Chief Operating Officer (Principal Financial Officer and Principal Accounting Officer)</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        John E. Alexander</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">John
        E. Alexander</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        Paul J. Battaglia</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Paul
        J. Battaglia</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        Daniel J. Fessenden</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Daniel
        J. Fessenden</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        Susan A. Henry</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Susan
        A. Henry</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        Patricia A. Johnson</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Patricia
        A. Johnson</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        Frank C. Milewski</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Frank
        C. Milewski</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        Michael H. Spain</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Michael
        H. Spain</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        Alfred J. Weber</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Alfred
        J. Weber</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0; text-align: left; vertical-align: top"><P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>/S/
        Craig Yunker</U></FONT></P>
        <P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Craig
        Yunker</FONT></P></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; font: 10pt Times New Roman, Times, Serif; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD>
    <TD STYLE="padding: 3pt 5.4pt 5.4pt; text-align: center; font: 10pt Times New Roman, Times, Serif; vertical-align: top; text-indent: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><U>January
    24, 2019</U></FONT></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; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>&nbsp;</B></FONT></P>

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

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>&nbsp;</B></FONT></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; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="width: 0.5in; font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><A HREF="ex5.htm">5</A></FONT></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Opinion
                                         of Harris Beach PLLC</FONT></TD></TR>                                                                              <TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>

<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><A HREF="ex23-1.htm">23.1</A></FONT></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Consent
                                         of KPMG LLP</FONT></TD></TR>                                                                     <TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>

<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><A HREF="ex5.htm">23.2</A></FONT></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Consent
                                         of Harris Beach PLLC (included in Exhibit 5)</FONT></TD></TR>                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                          <TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif"><A HREF="#powerofattorney">24</A></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">Power
of Attorney (included at Page II-2)</TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>
<TR STYLE="vertical-align: top; font: 10pt Times New Roman, Times, Serif">
<TD STYLE="font: 10pt Times New Roman, Times, Serif"><A HREF="http://www.sec.gov/Archives/edgar/data/1005817/000101905609001240/ex99.htm" STYLE="-sec-extract: exhibit">99</A></TD><TD STYLE="font: 10pt Times New Roman, Times, Serif">Tompkins
                                         Financial Corporation Employee Stock Ownership Plan (incorporated by reference to Exhibit
                                         99 to the Registrant&rsquo;s Registration Statement on Form S-8 (SEC Registration No.
                                         333-163977) filed on December 23, 2009).</TD></TR>
</TABLE>

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


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</HTML>
[{"type": "S-8", "sequence": "1", "filename": "tmp-s8_013119.htm", "description": "INITIAL REGISTRATION STATEMENT", "secsgml_size_bytes": 66102}]
{"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": "333-229469", "film-number": "19558039"}, "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
February 1, 2019
SEC
Registration No.
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 St.
Ithaca,
New York 14851
(Address
of Principal Executive Offices) (Zip Code)
TOMPKINS
FINANCIAL CORPORATION EMPLOYEE STOCK OWNERSHIP PLAN [ESOP]
(Full
title of the plan)
Francis
    M. Fetsko
with
    a copy to:
Executive
    Vice President, Chief Operating Officer
Alyssa
H. Fontaine, Esq.
And
    Chief Financial Officer
EVP
    & 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",
"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, $0.10 par value
125,000
$73.86
$9,232,500
$1,118.98
(1)
The
                                         Registration Statement also includes an indeterminate number of additional shares that
                                         may become issuable pursuant to share splits, share dividends, antidilution provisions
                                         and other adjustments to the extent contemplated by the Tompkins Financial Corporation
                                         Employee Stock Ownership Plan (the "ESOP").
(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 January 28, 2019.
EXPLANATORY
NOTE
Pursuant
to General Instruction E of Form S-8, this Registration Statement on Form S-8 (this "Registration Statement"), which
incorporates by reference the contents of the Registrant's previous Registration Statements on Form S-8 (No. 333-163977),
filed with the Securities and Exchange Commission on December 23, 2009; (No. 333-184582), filed with the Securities and Exchange
Commission on October 24, 2012; (No. 333-206043), filed with the Securities and Exchange Commission on August 3, 2015 (together,
the "Prior Registration Statements"), is being filed by the Registrant solely to register an additional 125,000 shares
for issuance under the Tompkins Financial Corporation Employee Stock Ownership Plan [ESOP]. The Prior Registration Statements
relate to the same class of securities and the same plan. Accordingly, this Registration Statement consists only of those items
required by General Instruction E to Form S-8.
PART
II
INFORMATION
REQUIRED IN THE REGISTRATION STATEMENT
Item
8.
Exhibits.
EXHIBIT
INDEX
The
following exhibits are filed with this Registration Statement:
5
Opinion
                                         of Harris Beach PLLC
23.1
Consent
                                         of KPMG LLP
23.2
Consent
                                         of Harris Beach PLLC (included in Exhibit 5)
24
Power
of Attorney (included at Pages II-2 and II-3)
99
Tompkins
                                         Financial Corporation Employee Stock Ownership Plan (incorporated by reference to Exhibit
                                         99 to the Registrant's Registration Statement on Form S-8 (SEC Registration No.
                                         333-163977) filed on December 23, 2009).
II-
1
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 24
th
day
of January, 2019.
TOMPKINS
FINANCIAL CORPORATION
By:
/s/ Stephen S. Romaine
Stephen
S. Romaine
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 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
Thomas
        R. Rochon
Chairman
    of the Board, Director
January
    24, 2019
/S/
Stephen S. Romaine
Stephen
        S. Romaine
President
    and Chief Executive Officer, Director
(Principal Executive Officer)
January
    24, 2019
/S/
        James W. Fulmer
James
        W. Fulmer
Vice
    Chairman, Director
January
    24, 2019
/S/
        Francis M. Fetsko
Francis
        M. Fetsko
Executive
    Vice President, Chief Financial Officer, Chief Operating Officer (Principal Financial Officer and Principal Accounting Officer)
January
    24, 2019
/S/
        John E. Alexander
John
        E. Alexander
Director
January
    24, 2019
/S/
        Paul J. Battaglia
Paul
        J. Battaglia
Director
January
    24, 2019
/S/
        Daniel J. Fessenden
Daniel
        J. Fessenden
Director
January
    24, 2019
/S/
        Susan A. Henry
Susan
        A. Henry
Director
January
    24, 2019
/S/
        Patricia A. Johnson
Patricia
        A. Johnson
Director
January
    24, 2019
/S/
        Frank C. Milewski
Frank
        C. Milewski
Director
January
    24, 2019
/S/
        Michael H. Spain
Michael
        H. Spain
Director
January
    24, 2019
/S/
        Alfred J. Weber
Alfred
        J. Weber
Director
January
    24, 2019
/S/
        Craig Yunker
Craig
        Yunker
Director
January
    24, 2019
II-
2
EXHIBIT
INDEX
5
Opinion
                                         of Harris Beach PLLC
23.1
Consent
                                         of KPMG LLP
23.2
Consent
                                         of Harris Beach PLLC (included in Exhibit 5)
24
Power
of Attorney (included at Page II-2)
99
Tompkins
                                         Financial Corporation Employee Stock Ownership Plan (incorporated by reference to Exhibit
                                         99 to the Registrant's Registration Statement on Form S-8 (SEC Registration No.
                                         333-163977) filed on December 23, 2009).