"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....I have directed the Surveyor early in the next Spring to ascertain the precise distance of the several Routes . . . and hope to compleat the Military Street or Road the ensuing Autumn." Lieutenant-Governor John Graves Simcoe to Secretary of State Henry Dundas, October 19, 1793

Simcoe proposed the 'military street' as a strategic route to help protect Upper Canada from American invasion. According to local legend "the longest street in the world," Toronto's Yonge Street, its completion was announced on February 20, 1796.

The Toronto Passage on Lake Ontario, known by the native people as the Carrying Place Trail, was the site of Fort Rouillé, which was burned down in 1759 by its French garrison as it retreated from British forces. It was a minor site for trade and settlement, but became more important after the American Revolution.

Loyalists moving northward to British territory established settlements along the upper St Lawrence and lower Great Lakes, leading to the creation of Upper Canada and the establishment of the town of York, now known as 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 if America decided to support its French allies. He transferred the capital to Toronto Bay, and founded York as the capital. It was a good position for a naval and garrison base. York's garrison and status as the capital attracted merchants, craftsmen and labourers, and surrounding agrarian settlement made it a local market centre.

Simcoe planned major roads, knowing their value for defence and for expanding development. Governor's Road (Dundas Street) would run west to the Detroit River and the second road, Yonge Street, would go north to the Holland River, creating a link with Georgian Bay on Lake Huron and Michilimackinac. A third, Danforth, would run east.

John Graves Simcoe, Yonge Street
Simcoe named the military route Yonge Street after Sir George Yonge, a family friend (courtesy Canadian Heritage Gallery).

Simcoe strengthened his proposal for the military route by pointing out its commercial advantages, telling Dundas that the "produce of the Lands on this Communication will in no distant period be sufficient to supply the North West Trade with such provisions as it may."

Simcoe set off on September 25, 1793 with a group of soldiers and native guides to explore north of Lake Ontario, following the Carrying Place Trail, a portage route running 45 km from Lake Ontario to Lake Simcoe, following the Humber and Holland Rivers. The trail was a necessary route, since the Humber's shallow water 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 as they set out 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, who supported the proposed project.

Simcoe's strategic route did not follow the natural contours of the land. It was truly a military road, running as straight as an arrow 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.

Yonge Street
King St. E. (south side between Yonge and Church Streets, looking east), 1856. Acquired with the assistance of a grant from the Minister of Communications under the terms of the Cultural Property Import & Export Review Act (Library and Archives Canada/PA-186739).

Augustus Jones, a United Empire Loyalist from New York State, was assigned the task of surveying and clearing the way. With the Queen's Rangers, Jones began the survey at Holland Landing and they worked their way south to York, cutting through the dense forest. 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.

Simcoe's York layout in 1793 was a small-town plot with a plain grid of straight streets along the eastern end of the harbour, with the garrison located westward. The straight-line grid expanded as the town grew, but by 1834 self-government had replaced planning with uncoordinated private developments. Today, the harbour front shore plain remains Toronto's downtown core and Simcoe's military street stretches some 1900 km.