| Document and Entity Information | Oct. 11, 2021 |
| Document and Entity Information | |
| Document Type | 8-K |
| Document Period End Date | Oct. 11, 2021 |
| Entity Registrant Name | WAYSIDE TECHNOLOGY GROUP, INC. |
| Entity File Number | 000-26408 |
| Entity Incorporation, State or Country Code | DE |
| Entity Tax Identification Number | 13-3136104 |
| Entity Address, Address Line One | 4 Industrial Way West, Suite 300 |
| Entity Address, City or Town | Eatontown |
| Entity Address, State or Province | NJ |
| Entity Address, Postal Zip Code | 07724 |
| City Area Code | 732 |
| Local Phone Number | 389-0932 |
| Title of 12(b) Security | Common stock, $.01 par value |
| Trading Symbol | WSTG |
| Security Exchange Name | NASDAQ |
| Entity Central Index Key | 0000945983 |
| Amendment Flag | false |
| Entity Emerging Growth Company | false |
| Written Communications | false |
| Soliciting Material | false |
| Pre-commencement Tender Offer | false |
| Pre-commencement Issuer Tender Offer | false |
