“Why we do it is a mystery,” says Nicholas Brinckman. “There is no reason to walk across the city carrying a canoe on your back. It’s madness.”

On Nov. 15, Brinckman and others will be doing just that for an event they call the Davenportage, a 17-kilometre portage between the Humber and Don Rivers.

The bulk of their route follows Davenport, one of Toronto’s oldest roads that roughly traces an even older First Nations trail called Gete-Onigaming, or “the old portage.”

Davenport also passes south of the shoreline of ancient Lake Iroquois, the former expanded glacial version of Lake Ontario, today a prominent escarpment running across the middle of Toronto between Davenport and St. Clair that is the bane of all north-peddling cyclists.

Brinckman and a few other colleagues were working together in a shared office in Yorkville when they came up with the idea to do a long walk that both explored the city and honoured some of its history.

“It’s a profound way to be in the city,” he says. “It made me feel more connected to this place.”

The first Davenportage was last year with a handful of guys.

“We thought we could have some fun and bring some attention to the trail,” says Michael Bumby, one of the co-founders.

“We first planned to just carry some heavy stuff in sacks, like potatoes or seed, the canoe came later. People were saying, ‘you guys are crazy,” so we thought, ‘OK, we’ll add the canoe.’ ”

This year, they expect a few more canoe teams and some younger portagers as well. Members of each team take turns carrying the canoe, something that gets a lot of attention along the way.

“When I went down to Mountain Equipment Co-op and told them I wanted to borrow a canoe for this, the reaction I got was really positive,” says Bumby. “Walking back to my office at Avenue and Bloor was really fun. People were yelling out of trucks “you need a hand?” Everybody relates to a canoe in some way.”

An acquaintance of Bumby’s from the Temagami First Nation in Northern Ontario thought it was a great idea and gave him some words to say during a tobacco ceremony at the beginning and end of the journey, which starts at noon in Etienne Brule Park, just north of the Old Mill Bridge.

From there, the Davenportage will walk north along the east bank of the Humber River to Dundas St., where it will head out of the valley and follow Dundas St. to Scarlett Rd. After a short jog north to St. Clair Ave., it will head east to Old Weston Rd. and then south to Davenport, which it will follow all the way to Yonge St. From there, a zig-zag route through Rosedale takes the hikers to Mt. Pleasant Rd., where they will connect to the belt line trail and the Evergreen Brickworks.

Bumby concedes the route deviates somewhat from the original First Nations trail, due to modern development. Along the way, they will stop at the Tollkeepers Cottage at Davenport and Bathurst. Now a community museum, it dates to the mid-1800s when Davenport and other roads were tolled, perhaps a precedent for the current debate about tolling expressways.

The Davenportage is a walk through an incredible amount of Toronto history and geography.

“Until you do it with your feet, you haven’t learned a lot about the land,” says Bumby. “That distance has not changed in 10,000 years. You can’t sense it in a car.”

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The Davenportage is accepting more teams, but it’s a bring-your-own-canoe event. See davenportage.ca for details.

Shawn Micallef writes every Friday about where and how we live in the GTA. Wander the streets with him on Twitter @shawnmicallef.

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