[1] It is one of the original streets in the old city of York, Upper Canada.

It starts at Queen's quay, and heads north to South Drive.

In 1838, following the Upper Canada Rebellion, seven blockhouses were built, guarding the approaches to Toronto, including the Sherbourne Blockhouse, built at the current intersection of Sherbourne and Bloor.

In the 19th Century Sherbourne was lined with the stately homes of many of Toronto's most prominent families, but by the 20th Century the remaining stately houses, like 230 Sherbourne Street, had been converted to rooming houses.

In the early 2000s City Council chose Sherbourne as one of the first streets in Toronto to be retrofitted with dedicated bike lanes.