1793, A Forgotten Trail Inspires Ontario’s Main Street

This John Graves Simcoe portrait was painted by Jean Laurent Mosnier and is reproduced courtesy of the Toronto Public Library’s Digital Archive.

On October 13, 1793, North Toronto was an endless maze of beech and pine trees, populated by deer, bears and wolves. The only sign of civilization in the neighbourhood was an almost forgotten Indian trail near the Don River – running through today’s Rosedale Golf Club.

Unlike the busy Carrying Place Trail near the Humber River, the trail through North Toronto was limited to use by Mississauga Indians fishing for salmon in the various rivers. In earlier times, it was likely a route used by Iroquois raiding parties, the coureurs-de-bois (French voyageurs) and Jesuit missionaries.

On this particular day it was being travelled by a small party led by the new Lieutenant-Governor of Upper Canada, John Graves Simcoe. ‘Led’ might not be the right word, because the group was often lost, stumbling off the vague pathway only to find it again a few hours later.

They were returning from a two-week trek exploring the trails and canoe route as far north as Lake Huron. An Ojibway, Old Sail, had told Simcoe about this forgotten trail south of Lake Simcoe that was a more direct route to Lake Ontario than the Carrying Place Trail.

And now they were down to their last day of food, concerned they might not make it back to Fort York on Lake Ontario. It’s likely some in the group – which included surveyor Alexander Aitkin, a small survey crew and a few Indians – were wondering just what they were doing here. Wet, cold, hungry and discouraged, the party pitched camp near the Don (probably in the vicinity of Glendon College).

The next morning, they came across a surveyor’s marker in the woods for the 4th Concession (now Eglinton Avenue). They knew where they were! By the end of the day they were back at Fort York.

The trail had been a twisting – at times invisible—pathway. But Simcoe knew he had the military route he wanted to Lake Simcoe and, ultimately, Lake Huron. He was determined to push a road, straight as an arrow, up to Lake Simcoe, using the path as a guide.

Aitkin, who had drawn maps and kept a journal along the way, had already had plenty of practice imposing rigid British survey grids onto the irregular landscape of Ontario. In fact, he laid out the first town plan for Toronto. Architectural author Eric Arthur has described Aitkin’s square-block grid for the new capital city as “practical, but indescribably mean and unimaginative”. It quite simply defied the hills and ravines that dotted the area.

Now Aitkin, along with surveyor Augustus Jones (the one who had placed that survey marker at the 4th Concession), began plotting the ramrod road through the bush that would become Yonge Street.

Gary Schlee has been a resident of Bedford Park since 1991. As an author and historian, he has written many articles about the history of our area, notably from 2003 – 2012, for Community Life published by Fairlawn Avenue United Church (FAUC). This article originally appeared in the Summer 2003 issue. BPRO is grateful to Gary and FAUC for kindly and generously authorizing us to reprint these articles on our website. Please come back regularly to see additional articles as we post them.