This ski club has quietly maintained wilderness trails for 50 years

Every Sunday throughout winter, a coach bus leaves Toronto just after 8 a.m., carrying skiers, nature lovers and adventure seekers deep into Crown land in the Muskoka and Gibson River forests.

The group is a mixed bag of professionals and personalities, aged 20 to 80, who are part of Five Winds Backcountry Ski and Snowshoe Club, a nonprofit volunteer organization that, for more than half a century, has quietly maintained more than 200 kilometres of wilderness trails between Gravenhurst and Georgian Bay.

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In a province where winter recreation often means chairlifts, grooming machines and pricey day passes, Five Winds has preserved an older, more elemental form of skiing: cross-country travel through untracked forest, powered by camaraderie, grit and shared knowledge of handmade trails.

“Many of our members have been skiing these routes for decades, bridging generations and keeping a small piece of classic Canadian winter culture from fading away,” says Jeff Mooallem, the club’s director. A semi-retired fintech manager, Mooallem met his wife, Linda, through Five Winds more than 30 years ago.

Now the 62-year-old worries about the club’s future.

“As many of our longtime members age – and fewer people know that this kind of backwoods skiing exists near Toronto – the tradition itself risks disappearing,” Mooallem says. Before the pandemic, the bus regularly carried 60 to 80 skiers and snowshoers north each week. These days, it averages 30.

“What began as a group of outdoor dreamers in the 1970s is now one of the last volunteer clubs with its own wilderness trail network in southern Ontario,” he says. “It is a legacy worth protecting and preserving.”

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Five Winds began with founder Michael Naughton, a British Army officer and former commando during the Second World War. After moving to Toronto in the 1950s, Naughton became an avid explorer of the province’s forests, rivers and lakes, particularly in what is now Gibson River Provincial Park.

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In the 1960s, Naughton met Herman (Jackrabbit) Smith-Johannsen, a Norwegian-born ski pioneer largely credited with popularizing cross-country skiing in North America. Smith-Johannsen, who lived to be 111, had already blazed hundreds of kilometres of trails around Saint-Sauveur in Quebec’s Laurentians. He was admired by many, including former prime minister Pierre Elliott Trudeau, who called Smith-Johannsen “an inspiration and an outstanding example of what a healthy and active life can bring in terms of vigour and well-being.”

The meeting left a lasting impression on Naughton, who persuaded a small group of friends to drive north on weekends to bushwhack ski trails through Muskoka’s largely untouched forests. Five Winds was officially formed in 1973, and over time, members expanded and refined the network that the club still uses today.

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Unlike commercial ski centres, Five Winds offers no grooming, signage or fixed routes. Conditions change in tandem with freeze-thaw cycles. Many newcomers start on snowshoes, learning how to properly layer clothing, read terrain and navigate changing conditions. As their confidence grows, many switch to skis, guided by veterans who teach them how to be nimble and light on the challenging terrain.

“The more experienced people teach the less experienced people,” says Kyra Bell-Pasht, a Toronto lawyer working in climate advocacy who joined Five Winds during the pandemic, drawn by a need for open spaces, physical exertion and human connection.

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“We share some of the most magical experiences and sights,” she says. “The land is so beautiful and pristine. We all feel very protective of it so we take care of it as best we can.”

Bell-Pasht skis groomed trails as well but says they don’t compare. “Skiing in controlled environments is great too, but it’s very different. You’re passing people all the time. It’s like walking on a sidewalk.

“On Five Winds trails you don’t see another soul, except the group you’re with. It’s total immersion in wilderness. Quiet. Unspoiled. The backwood trails feel like an escape. They regenerate me at a core level. They are exhausting, yes, but good exhausting.”

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That sense of stewardship extends beyond winter. Trail maintenance happens year-round. During shoulder seasons, members carpool to Muskoka to clear fallen trees, reroute sections and repair crossings. It’s labour-intensive, but social, too.

In spring and fall, Bell-Pasht often joins the clean-up crews, who combine maintenance duties with canoe camping, hiking, and activities like mushroom foraging. “I was hooked from the very beginning,” she says. “I fell in love with the landscape and what the club was all about – staying active, appreciating nature, and meeting people with shared interests.”

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Bell-Pasht first heard about Five Winds from a stranger she met while hiking the Bruce Trail. Recruitment has largely always worked that way. Today, the club has about 90 members who each pay $70 in annual dues ($50 for students).

For Mooallem, the reward lies in what can’t be planned or predicted. “We talk a lot about the sense of discovery,” he says. “Like when we come across a beaver dam, or look up and see heron nests, high in the treetops, while crossing a frozen marsh.

“I fear that many people are losing that sense of discovery,” he says. “People stay in controlled, manicured environments where there are no surprises. Out here, we feel like explorers. Like kids again.”

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