In 1793, the aristocratic Lieutenant-Governor of Upper Canada, Colonel John Graves Simcoe decided to move his seat of government at Niagra away from the danger of the American border. Previously, his regiment, the Queen's Rangers, had fought in the American war and he, himself, had been wounded and captured.

Simcoe chose a place across Lake Ontario where the Humber River branch of the Toronto Carrying-Place Trail met the lakeshore at Rousseau's trading post. There, Simcoe found good harbor and named his new outpost after the Duke of York. Northerly, the trail wound over the Oak Ridges Moraine to the Holland River and the lake (Simcoe). Across the lake, were trails to Georgian Bay on Lake Huron.

Recognizing its military and commercial value, Simcoe surveyed the Toronto Carrying-Place Trail in September 1793 while his Queen's Rangers were building the Huts at York. Upon his return, Simcoe planned a military road north to the lake and named it Yonge Street (pronounced "Young" Street) for his patron, Sir George, the Secretary of War. But it was 28 miles of primeval forest to clear, 20 feet wide!

The route from York to Lake Simcoe was surveyed by Stegman and at Simcoe's order, the Queen's Rangers began construction of Yonge Street in the spring of 1794. They had reached lot #29 in Thornhill by August when they were ordered away to the defence of Fort Miami, near Detroit.

Why did they come? Free land is the short answer, overpopulation is the hidden reason. When land values overwhelm the capacities of young families, they wander. Other possibilities are opportunity, and speculation. They'd hoped for opportunity and found speculation in the New York Military Tracts, sold their farms and gambled that they could do it again. Philip 55 sold his share of Lot #83 to James 51 and moved south to Etobicoke and built a tavern.

Meanwhile in the United States, Quakers were discontented with the reckless and sinful ways of the new republic and were looking for refuge where they could be free of slavery and the threat of Indian war. In the winter of 1800 the Quaker, Timothy Rogers, came scouting prospects in Upper Canada and found settlers already in residence.