In 1793, Dundas Street was assessed for a military road. In 1805, the Legislative Assembly of Upper Canada bought the area between Etobicoke and Hamilton from the Mississaugas aboriginal people, leaving out the land at the edge of Twelve Mile Creek (Bronte Creek), Sixteen Mile Creek, and along the Credit River.

The native harbor at Bronte was an essential port of entry for merchants and sailors in the early 1800’s. In 1827, Colonel William Chisholm obtained land at the mouth of the Sixteen Mile Creek on Lake Ontario to establish a shipbuilding yard.

Oakville's first industries incorporated shipbuilding, timber shipment, and wheat farming. In the 1850s, there was an economic stagnation and the foundry, the largest industry in town, was closed. Basket-making became a main industry in the town.

In 1962 the town of Oakville combined with its adjoining villages (Bronte, Palermo, Sheridan, and the remainder of Trafalgar Township) to become the new Town of Oakville, reaching northwards to Steeles Avenue in Milton.