<SEC-DOCUMENT>0001415889-22-006195.txt : 20220607
<SEC-HEADER>0001415889-22-006195.hdr.sgml : 20220607
<ACCEPTANCE-DATETIME>20220607144412
ACCESSION NUMBER:		0001415889-22-006195
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20220603
FILED AS OF DATE:		20220607
DATE AS OF CHANGE:		20220607

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Foster Dale Richard
		CENTRAL INDEX KEY:			0001545927

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	000-26408
		FILM NUMBER:		221000945

	MAIL ADDRESS:	
		STREET 1:		10900 PUMP HOUSE ROAD
		CITY:			ANNAPOLIS JUNCTION
		STATE:			MD
		ZIP:			20701

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			Wayside Technology Group, Inc.
		CENTRAL INDEX KEY:			0000945983
		STANDARD INDUSTRIAL CLASSIFICATION:	WHOLESALE-COMPUTER & PERIPHERAL EQUIPMENT & SOFTWARE [5045]
		IRS NUMBER:				133136104
		STATE OF INCORPORATION:			DE
		FISCAL YEAR END:			1231

	BUSINESS ADDRESS:	
		STREET 1:		4 INDUSTRIAL WAY WEST
		STREET 2:		SUITE 300
		CITY:			EATONTOWN
		STATE:			NJ
		ZIP:			07724
		BUSINESS PHONE:		732-389-0932

	MAIL ADDRESS:	
		STREET 1:		4 INDUSTRIAL WAY WEST
		STREET 2:		SUITE 300
		CITY:			EATONTOWN
		STATE:			NJ
		ZIP:			07724

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	PROGRAMMERS PARADISE INC
		DATE OF NAME CHANGE:	19950531
</SEC-HEADER>
<DOCUMENT>
<TYPE>4
<SEQUENCE>1
<FILENAME>form4-06072022_110602.xml
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0306</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2022-06-03</periodOfReport>

    <issuer>
        <issuerCik>0000945983</issuerCik>
        <issuerName>Wayside Technology Group, Inc.</issuerName>
        <issuerTradingSymbol>WSTG</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001545927</rptOwnerCik>
            <rptOwnerName>Foster Dale Richard</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>4 INDUSTRIAL WAY WEST</rptOwnerStreet1>
            <rptOwnerStreet2>SUITE 300</rptOwnerStreet2>
            <rptOwnerCity>EATONTOWN</rptOwnerCity>
            <rptOwnerState>NJ</rptOwnerState>
            <rptOwnerZipCode>07724</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>true</isDirector>
            <isOfficer>true</isOfficer>
            <isTenPercentOwner>false</isTenPercentOwner>
            <isOther>false</isOther>
            <officerTitle>CEO</officerTitle>
            <otherText></otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2022-06-03</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>S</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>1708</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>37.75</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>66841</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value></value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2022-06-03</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>S</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>10</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>38.03</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>66831</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value></value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2022-06-06</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>S</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>1282</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>37.75</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>65549</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value></value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <derivativeTable></derivativeTable>

    <footnotes></footnotes>

    <ownerSignature>
        <signatureName>/s/ Dale Foster</signatureName>
        <signatureDate>2022-06-06</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
