How Oakville Began: A brief history of the founding of Oakville Back in the 1700s, the town we now know as Oakville was then the home of the Mississauga First Nation who farmed on the fertile lands around Sixteen Mile Creek.
In 1793, a military road (now Dundas Street) linking Lakes Ontario, Erie, St Clair and Huron was proposed by Lieutenant Governor John Graves Simcoe. Around this time, a growing number of United Empire Loyalists were moving to the area, fleeing the United States after the American Revolution.
In 1805, with an increasing demand for land, the Crown purchased the land from Etobicoke Creek through to Burlington Bay from the Mississauga First nation. Know as the Mississauga Purchase, it left the Mississauga First nation with blocks of land around the mouths of the three rivers, including 960 acres at Sixteen Mile Creek.
The following year, the Crown surveyed the lands and created the townships of Trafalgar, Nelson and Toronto. Using Dundas Street as a reference line, the land was split into 200-acre lots. Oakville’s first settlers were predominantly Irish, English and Scottish.
By 1820, the Mississauga First Nation sold their remaining reserve lands to the Crown. That area would soon catch the interest of a successful businessman, shipbuilder and politician named William Chisholm who lived in nearby Burlington Bay.
 William was the son of George Chisholm, a United Empire Loyalist who had moved his family from Nova Scotia to Burlington Bay in 1794. William fought as a lieutenant in the War of 1812. After the war, Chisholm resumed his business and was purchasing timber and white oak staves throughout the district between Burlington Bay and the Credit.
With a keen interest in developing the lovely natural harbour, he purchased 960 acres of land around the mouth of Sixteen Mile Creek in 1827 and immediately began construction on the first privately owned harbour in Upper Canada. The village was named Oakville, and it soon had a shipbuilding yard, sawmill, gristmill and warehouses.
William placed his son, Robert Kerr, and his brother-in-law, Merrick Thomas, in charge of laying out and building the new the town. In 1834, Oakville was declared a port of entry. A Customs House was established. Upon William’s death in 1842, Robert Kerr ran the customs house as well as the post office from the Erchless house he constructed at the foot of Navy Street.
The village continued to prosper, and in 1857 it was designated a Town. George King Chisholm, the eldest son of founder William, was its first mayor. |