In 1793, Dundas Street was surveyed for a military road. In 1805, the Legislative Assembly of Upper Canada bought the lands between Etobicoke and Hamilton from the Mississaugas aboriginal people, except for the land at the mouths of Twelve Mile Creek (Bronte Creek), Sixteen Mile Creek, and along the Credit River. In 1807, British immigrants settled the area surrounding Dundas Street as well as on the shore of Lake Ontario.
In 1820, the Crown bought the area surrounding the waterways. The area around the creeks, 960 acres (3.9 km2), ceded to the Crown by the Mississaugas, was auctioned off to William Chisholm in 1827. He left the development of the area to his son, Robert Kerr Chisholm and his brother-in-law, Thomas Merrick.
Oakville's first industries included shipbuilding, timber shipment, and wheat farming. In the 1850s, there was an economic recession and the foundry, the most important industry in town, was closed. Basket-making became a major industry in the town, and the Grand Trunk Railway was built through it.
The town eventually became industrialized with the opening of Cities Service Canada (later BP Canada, and now Petro Canada) and Shell Canada oil refineries (both now closed), the Procor factory (no longer manufacturing), and, most importantly, the Ford Motor Company's Canadian headquarters and plant, all close to the Canadian National Railway and the Queen Elizabeth Way highway between Toronto and Fort Erie (Buffalo).
In 1962 the town of Oakville merged with its neighbouring villages (Bronte, Palermo, Sheridan, and the remainder of Trafalgar Township) to become the new Town of Oakville, reaching northwards to Steeles Avenue in Milton. In 1973, the restructuring of Halton County into Halton Region brought the northern border southwards to just north of the future Highway 407.