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Settlers were attracted to this area in the early 1800's due to rich timber resources and water-power potential. The river was once known as the Tanaouate and formed part of the route known as the Carrying Place Trail (a native trading path) which paralleled the Humber River following its eastern tributaries north-east to the Holland River and Lake Simcoe.
In 1806 the first sawmill was established on the west side of the river. The following 2 decades saw the growth of the small hamlet, initially referred to as "The Humber", in the river valley close to the mill site. About 1815 millers James and John Farr took over operation of what was then a grist and saw mill and renamed the small community Weston after their English home. The community expanded to both banks as a distillery, blacksmith shop, harness maker, cooper shop, tavern and other amenties were built.
A flood destoryed the river valley settlement in 1850. The grist mill now owned by the Wadsworth brothers was rebuilt and operated into the early 20th century.
After the flood, Weston was rebuilt chiefly on the high, east bank. The arrival of the railway (1856/1869) ensured Weston's continued growth. Fires and floods deastoryed most of the mills. Over the years steam power gradually replaced water power.
Weston was incorporated as a village in 1881 and as a town in 1915. By WW ll Weston was the commerical hub for the area northwest of Toronto.
Hurricane Hazel wreaked havoc in 1954 as 7.2 inches of rain fell in 24 hours. The Humber River rose 30 feet. Numerous homes were lost on Maple Bush Drive, Fairglen Crescent and Dee Avenue. On Raymore Drive thirty-six people lost their lives, 60 families were left homeless and 1200 feet of street disappeared.
Weston because part of the Borough of York in 1967 and was one of the 6 municipalities amalgamated into the new City of Toronto in 1998.
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