Cooksville was originally located in Toronto Township, and was an important stagecoach stop along the Dundas highway,[citation needed] which was carved out of the wilderness after a survey by Asa Danforth Jr. in 1798.

[3] The entrepreneur, Jacob Cook, won the contract to deliver mail from York to Niagara, operated several stage coach lines, was the local magistrate and built the Cooksville House, the first licensed tavern in the area at the northwest corner of Dundas and Hurontario streets in 1829.

Although never incorporated and not being the city's largest historic community, its central crossroads location meant much of the early suburban growth in Mississauga (Toronto Township before 1967)[6] occurred in the area around Cooksville.

Cooksville is a main transportation hub in Mississauga, with GO Transit rail, and bus service; and express city buses to Toronto's Union Station.

The area in the southwest part of Cooksville, closer to the Credit River, is a more exclusive enclave of mostly large, detached homes on larger, treed lots; is referred to as Gordon Woods.