In the 1790's Weston was a tiny hamlet known simply as "The Humber". The area rich timber resources and the water-power potential of the Humber River magnetized the first mill owners.

The Weston name is connected to the Wadsworth brothers who came to this area in 1828 and invested in a local flour mill and general store. They renamed this community Weston after their familial home in Weston-super-Mare, Somerset, England.

Weston's early advancement took place on both sides of the Humber River. First the Grand Trunk Railway (1856) and then the Toronto Grey and Bruce Railway (1869) began service to this area. The railway and related industry brought considerable growth to Weston.

Weston was first integrated as a village in 1881 and then as a town in 1915. Weston stayed an independent town until 1967 when it amalgamated with the former Borough of York, which is 1998 amalgamated with the City of Toronto.