The Very Beginning
Oakville's story commenced at 12:00 PM, Thursday, August 16, 1827 at Crook's Mill, Dundas Street and Twelve Mile Creek. A 968 acre portion of Trafalgar Township centred on the mouth of the Sixteen Mile Creek* was acquired at auction by William Chisholm. It was part of a large Crown Tract stretching from Twelve Mile Creek to the Credit River acquired by treaty with the Crown from "the five Principal Chiefs of the Mississagas" February 28, 1820.
The proceeds, $4,116 ($4.25/acre) were paid, over four years, in trust to the Commissioner for Crown Lands, Peter Robinson (whose name lives on, on the street one block south of Colborne Street (now Lakeshore) in old Oakville.
The trust was for the benefit of the Mississagas, who had moved to New Credit, where the Mississauga (note spelling difference) Golf Club now stands, to complete the building of their log houses.
Back at the mouth of the Sixteen, a construction program commenced that fall, and creation of a harbour to ship lumber, primarily white oak staves cut from the surrounding hardwood forest, commenced in the spring of 1828.
"It was a most favourable circumstance that the preceding and succeeding winters were mild, dry and open, with so little snow that the level of the lake was very low". (From Joseph Pickering, Inquiries of an Emigrant, London, 1831 - quoted by Mathews, below).
The small settlement grew and thrived on lumber and wheat exports to the US and UK, and shipbuilding. It was incorporated as a town in 1857.
Most of the foregoing is from the very detailed history of Oakville from its beginning to about 1950 by Hazel Mathews, a descendent of Chisholm, Oakville and the Sixteen - A History of an Ontario Port. A good read.
* Why the name Sixteen Mile Creek?
It's sixteen miles east of the opening connecting Lake Ontario with Hamilton Harbour. Bronte Creek, also known as Twelve Mile Creek, is four miles west of the Sixteen. Now you know.
Skipping forward to 1913, Cumberland Land Company, Limited released the Brantwood Survey, promising "beautifully located, healthful surroundings, inviting prospects, pleasing vistas, with city conveniences". It was Oakville's first significant expansion east (other than estates on the lake), bounded by Colborne, Allan, Spruce and Gloucester and comprised over 400 lots.
In addition to being a fascinating glimpse of Edwardian Oakville the brochure demonstrates how little, in many ways, real estate marketing has changed in a century.
May I present Brantwood!
Elsewhere, storm clouds were gathering in the world that would eventually spread even to this small town. Our cenotaph at George's Square on Trafalgar is a moving testament to what happened in subsequent years.
Oakville Historical Society
For more history here is a link to a presentation by Oakville Historical Society. Lots of material and good pictures of times past.