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Proc-Type: 2001,MIC-CLEAR
Originator-Name: webmaster@www.sec.gov
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 TWSM7vrzLADbmYQaionwg5sDW3P6oaM5D3tdezXMm7z1T+B+twIDAQAB
MIC-Info: RSA-MD5,RSA,
 OWad7Ti/zRxQabqL6c5TOCDjg0ZWXiFFfORgDqiwT8NYuQsw+BCRQZUdJYwYqeZO
 TcW1bD2yFto96O9b2AYfRw==

<SEC-DOCUMENT>0000894579-08-000341.txt : 20081112
<SEC-HEADER>0000894579-08-000341.hdr.sgml : 20081111
<ACCEPTANCE-DATETIME>20081112132753
ACCESSION NUMBER:		0000894579-08-000341
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20081105
FILED AS OF DATE:		20081112
DATE AS OF CHANGE:		20081112

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:		1157 SHREWSBURY AVE
		CITY:			SHREWSBURY
		STATE:			NJ
		ZIP:			07702
		BUSINESS PHONE:		7323898950

	MAIL ADDRESS:	
		STREET 1:		1157 SHREWSBURY AVE
		CITY:			SHREWSBURY
		STATE:			NJ
		ZIP:			07702

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	PROGRAMMERS PARADISE INC
		DATE OF NAME CHANGE:	19950531

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			JAMIESON DANIEL T
		CENTRAL INDEX KEY:			0001282872

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	000-26408
		FILM NUMBER:		081179938

	BUSINESS ADDRESS:	
		STREET 1:		1157 SHREWSBURY AVE
		CITY:			SHREWSBURY
		STATE:			NJ
		ZIP:			07702
		BUSINESS PHONE:		7323898950
</SEC-HEADER>
<DOCUMENT>
<TYPE>4
<SEQUENCE>1
<FILENAME>edgar.xml
<DESCRIPTION>PRIMARY DOCUMENT
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0303</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2008-11-05</periodOfReport>

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

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001282872</rptOwnerCik>
            <rptOwnerName>JAMIESON DANIEL T</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>1157 SHREWSBURY AVENUE</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>SHREWSBURY</rptOwnerCity>
            <rptOwnerState>NJ</rptOwnerState>
            <rptOwnerZipCode>07702</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>0</isDirector>
            <isOfficer>1</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
            <officerTitle>VP &amp; GM of Lifeboat</officerTitle>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2008-11-05</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>F</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>151</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>7.74</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>13697</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value></value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
        <nonDerivativeTransaction>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <transactionDate>
                <value>2008-11-05</value>
            </transactionDate>
            <transactionCoding>
                <transactionFormType>4</transactionFormType>
                <transactionCode>D</transactionCode>
                <equitySwapInvolved>0</equitySwapInvolved>
            </transactionCoding>
            <transactionAmounts>
                <transactionShares>
                    <value>45</value>
                </transactionShares>
                <transactionPricePerShare>
                    <value>7.74</value>
                </transactionPricePerShare>
                <transactionAcquiredDisposedCode>
                    <value>D</value>
                </transactionAcquiredDisposedCode>
            </transactionAmounts>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>13652</value>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
                <natureOfOwnership>
                    <value></value>
                </natureOfOwnership>
            </ownershipNature>
        </nonDerivativeTransaction>
    </nonDerivativeTable>

    <footnotes></footnotes>

    <remarks></remarks>

    <ownerSignature>
        <signatureName>/s/ Daniel T. Jamieson</signatureName>
        <signatureDate>2008-11-12</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
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