By Laura Neilson Bonikowsky
I have ascertained by a Route hitherto unknown but to some Indian Hunters, that there is an easy Portage between York and the Waters which fall into Lake Huron of not more than thirty miles in extent…. and hope to compleat (sic) the Military Street or Road the ensuing Autumn.”
~ Lieutenant-Governor John Graves Simcoe to Secretary of State Henry Dundas, October 19, 1793
John Graves Simcoe, first lieutenant-governor of Upper Canada, proposed the “military street” as a strategic route to help protect Upper Canada from American invasion.
The Toronto Passage on Lake Ontario, known by the First Nations as the Carrying Place Trail, was the site of Fort Rouillé, which was burned down in 1759 by French troops retreating from British forces. It was a minor site for trade and settlement, but gained importance after the American Revolution.
Loyalists moving northward to British territory established settlements along the upper Saint Lawrence and lower Great Lakes, leading to the creation of Upper Canada and the establishment of York (Toronto).
When war broke out between England and France in 1793, Simcoe realized that the capital Newark (Niagara-on-the-Lake) and its Lake Erie trade route would be vulnerable to attack should America support its French allies. He transferred the capital to Toronto Bay, establishing York as the capital, and planned major roads, both for defence and for expanding development. He strengthened his proposal for the military route by pointing out its commercial advantages as a trade route.
Simcoe embarked on Sept. 25, 1793, with a group of soldiers and Aboriginal guides to explore north of Lake Ontario, following the Carrying Place Trail portage route from Lake Ontario to Lake Simcoe and along the Humber and Holland Rivers. The trail was a necessary route, since the shallow Humber was often difficult to navigate, it froze solid in winter and its steep banks offered little defence against attack.
Simcoe and his party traversed the difficult marshland to Lac aux Claies, which he renamed Lake Simcoe to honour his father. He determined that the portage was an unsuitable route to Georgian Bay, perhaps because his guides got lost on the return trip. They returned from Holland Landing by way of Bond Lake and branches of the Don River. Simcoe had found his route and wrote with great excitement to Dundas.
Simcoe’s strategic route did not follow the natural contours of the land but was truly a military road, running arrow-straight from York to Holland Landing. Simcoe named the road Yonge Street, after Sir George Yonge, secretary of war in the British Cabinet and a family friend.
Augustus Jones, a United Empire Loyalist from New York State, was assigned to survey and clear the way. He and the Queen’s Rangers began at Holland Landing and worked their way through the dense forest south to York. The difficulty of clearing the road was partially solved by charging each settler along the route to clear six acres of land within 12 months, including a section of Yonge Street. Simcoe set convicted drunks to removing tree stumps as part of their sentences.
The completion of Yonge Street was announced on February 20, 1796.Today, what was once Simcoe’s military road stretches some 1,900 kilometres.
Today, what was once Simcoe’s military road is part of a road system that stretches some 1,900 kilometres and has been mythologized as the world’s longest street.
Laura Neilson Bonikowsky is associate editor of The Canadian Encyclopedia.
