For a moment, I forgot I was in the city.

Birdsong filled the air. Old trees leaned intimately over the water. There was the gentle splash of paddles, a pair of mallard ducks foraging on the shore, then, floating beside us, a translucent latex tube.

My guide, Toronto and Region Conservation Authority (TRCA) program manager Matt Kenel, looked at the condom and frowned.

“We like to encourage public use of our natural spaces …” he said, then trailed off.

“That’s neat, though. That could have been from a couple of kids up in Markham and it took three months to get down here.”

On Sunday, more than 600 paddlers took to the Don River for the 22ndPaddle the Don event, which raised some $100,000 for the protection, regeneration and conservation of the river. Hoping to challenge the waterway’s terrible (and somewhat deserved) reputation, the course saw paddlers meander 10.5 km from the lushly forested E.T. Seton Park to the trash-strewn waters of the Keating Channel.

“One of the key things about this event is to raise awareness that we’re a city of rivers,” Kenel said. “It enriches the entire city to have these places to go to.”

For thousands of years, the Don served as a First Nations thoroughfare. In the late 18th century, mills were constructed along its banks, heralding two centuries of abuse and neglect. As Toronto grew, the Don became increasingly industrialized. Meat processing plants, landfills, oil refineries and the sprawling Don Valley Brickworks began to overwhelm its ecosystem. People still joke that you could once set the river on fire by simply dropping a lighted match.

Conservation efforts began after World War II, and while the river is still far from its pristine original state, it has been faring better in recent years. Chinook salmon work their way upriver, hawks and robins dart overhead, beavers make dams and deer can be seen grazing along its banks.

But while heavy industry has largely disappeared from the Don, Toronto’s rapid urbanization has created a new set of problems. According to the TRCA, more than 1.2 million people call the Don River Watershed home. According to Environment Canada, the Don has the dirty distinction of being one of only three core waterways in the country with a “poor” water quality grade.

“It’s a natural space in a very urbanized area, so there are a lot of urban pressures on the river,” says Arlen Leeming, TRCA project manager for the Don and Highland watersheds.

Stormwater, Leeming says, is the chief concern today — not so much for the water itself, but for the sediment and pollutants it carries from our streets.

The Don usually isn’t navigable, Kenel says — it’s too shallow. But once a year, at 3 a.m. on event day, a reservoir is opened at Dufferin St. and Finch Ave. By 8 a.m., that water reaches E.T. Seton Park, raising the river by about 30 cm.

For the beginning of our trip, the river was tree-shaded and lovely. Rapids whisked us. Kenel fulfilled his promise to keep me dry. Other canoeists weren’t so lucky.

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Signs of human life became increasingly evident as we arrived at the Don’s lower reaches. The lush valley gradually gave way to relics of the river’s industrialized past: corroded metal reinforcements, abandoned graffiti-tagged railway bridges and crumbling concrete embankments.

At the Bloor Viaduct, a subway train rattled overhead. Old tires could be seen on the river’s bottom. Half-buried bicycles dotted its shore.

At one point, we saw a grey and red Target shopping cart protruding from the water.

“Well,” Kenel said. “That sums up the Canadian Target experience.”

Utility poles and apartment buildings increasingly poked above the river’s old trees, and the water gradually turned from clear cool brown to something thick and murky. The trees disappeared, and the river entered an artificially straightened channel that runs parallel to the deafening Don Valley Parkway.

There were more graffiti-tagged bridges. The filthy smell of the water filled our nostrils. Entering the Keating Channel, which connects the Don with Toronto’s inner harbour, the river took a sharp 90-degree turn, where swans nested and a landing party waited to congratulate us on our successful paddle.

Once, the Don met Lake Ontario via sprawling marshlands, Kenel said. The TRCA hopes to re-create a more natural mouth for the river.

“We haven’t always treated it in the best way,” Kenel said at the end of our trip, “but we’re slowly but surely fighting the good fight, fixing the damage and getting new generations out here.”

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