Weston's history dates back to the 1790's when it was a tiny hamlet known simply as "The Humber". Weston's first settlers were mill owners who were attracted to this area by its rich timber resources and the water-power potential of the Humber River.
The Weston name is attributed to the Wadsworth brothers who came to this area in 1828 and purchased a local flour mill and general store. They renamed this community Weston after their ancestral home in Weston-super-Mare, Somerset, England.
Weston's early development took place on both sides of the Humber River. However in 1850 a disastrous flood destroyed the west bank settlement. Weston's fortunes would take a turn for the better when first the Grand Trunk Railway (1856) and then the Toronto Grey and Bruce Railway (1869) began service to this area. The railway and associated industry brought great prosperity to Weston.
Weston was first incorporated as a village in 1881 and then as a town in 1915. Weston remained an independent town until 1967 when it amalgamated with the former Borough of York, which in 1998 amalgamated with the City of Toronto.
Weston still looks and feels more like a small Ontario town than a big city neighbourhood. This is not surprising considering the two dominant features in Weston's history the Humber River and the Railway, are still important landmarks in this community.
Weston's abundant civic pride is evident along Weston Road, which serves as the main street in the neighbourhood. Large green and gold road signs on Weston Road welcome visitors to this community. Weston Road also serves as the parade route for the annual Weston Santa Clause Parade.