After the American Revolutionary War, many United Empire Loyalists settled in the fertile region along Lake Ontario's shores. In the early 1800's, the Hudson Bay Company established a storehouse on what is now Kempenfelt Bay on Lake Simcoe.
In the 1790s, Lieutenant Governor John Graves Simcoe began the constuction of Yonge Street (named for the British Secretary of War, at the time) northwards from Toronto to connect to Lake Simcoe via Holland Landing and Thornhill. This road was made of logs laid across the cleared land (a "corduroy" road).
During the War of 1812, the town became strategic when the Americans sank the Schooner Nancy to cut the British supply line to Fort Michillimacinac and points to the north and west.
The Nine Mile Portage became important in the War of 1812 after the Americans at Detroit controlled the St. Clair River, and marine access to the upper Great Lakes. The British enlarged the Nine Mile Portage to accommodate wagons to move supplies and troops from Upper Canada to military posts on Lake Huron and Lake Superior.
More history of Barrie-Muskoka