Keep on rolling Two Winnipeggers lace up to wheel joyfully into 2025 for the challenge and health benefits, but mostly for fun By: Eva Wasney and Ben Waldman Posted: 11:35 AM CST Friday, Jan. 3, 2025

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This article was published 03/01/2025 (622 days ago), so information in it may no longer be current.

It’s a new year. A time swirling with possibility, hope and visions of self-improvement.

For two Winnipeg strangers with a tandem passion for roller skating, 2025 is the end of a year spent doing something they love in spite of inclement weather, waning motivation and internet nastiness.

Their stories differ, but both offer timely reminders about the importance of seeking joy and embracing vulnerability.

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“I’m most comfortable on skates,” Dave Rider quips while coasting through his living room on a pair of blue roller skates with bubblegum pink wheels. He swerves deftly around the ottoman before settling into the couch.

This week Rider, 52, completed a major personal goal: skating at least an hour every day for an entire calendar year.

It’s an achievement that started casually when he realized he had been rolling daily for the first few days of 2024. A week in, he decided to see how long he could keep it up.

“I’m pretty happy about it,” he says with a hint of a shrug.

Rider is proud of his consistency, but isn’t one to boast. He’s also quick to clarify the accomplishment as a “skating challenge” since, technically, eight of those 365 days were spent ice skating.

Born and raised in Winnipeg, Rider is the youngest of seven siblings and a single dad of two grown children. He’s been roller skating voraciously since 2021, when he happened upon a video of the Peg City Rollers — a group of local skating enthusiasts who meet regularly to practise moves and cruise around the city together.

“The pandemic was just opening up and I was looking for something fun to do,” he says. “I bought a pair of skates and joined.”

A lifelong ice skater who enjoys dancing, Rider was immediately hooked. The music, the movement, the community of like-minded people — it was exactly the fun he was looking for.

In his first year with Peg City, Rider was voted “Most Badass Skater” for his tendency to approach new moves and challenging tricks without hesitation. He’s currently working on landing a flip out of the bowl at The Forks’ skatepark.

“I didn’t mind falling,” he says. “You fall and you learn and you get up and do it again.”

It’s a statement that sounds like a life philosophy, but Rider insists roller skating, for him, isn’t so deep. “It’s just fun,” he says with a laugh.

Living in a city with months of snow meant Rider, a tire technician who works early mornings, had to get creative to meet his goal of skating an hour or three every afternoon.

During the summer, he cruised downtown Winnipeg and frequented outdoor basketball courts and skateparks. Come winter or bad weather, he joined the Peg City Rollers for indoor sessions at Wheelies Roller Rink or a local dance studio.

Rider also logged plenty of hours in the spare bedroom of his second-floor apartment; however, he only skates at home when he knows his downstairs neighbours are away.

Over the last year, he’s been posting his daily outings on social media and had one TikTok video go viral after it was shared by an overseas influencer. Save for a few negative comments, which he promptly deletes, the response from friends, family and passersby has been overwhelmingly positive.

Not that it matters, though. Like roller skating itself, documenting the process is something Rider does for his own enjoyment — and perhaps a wicked future memorial video.

“I joke with people that I’m (sharing) it online, so when I die I’ll have a pretty awesome funeral,” he says.

After skating for a year straight, Rider says his fitness has improved greatly, he’s sleeping better and has more friends.

Still, some days it was hard to find the motivation to lace up. His friend Yvette, a fellow Peg City Roller, helped get him out the door on many occasions, as did a simple mantra — one he offers up to anyone apprehensive about starting a new hobby, roller skating or otherwise.

“Don’t be afraid,” he says. “Just get out there and do it.”

-Eva Wasney

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After psychiatric nurse Stephanie Cleveland spends an eight-hour shift on her feet, she heads outside to spend an hour or so on her toes, rocking back and forth to an invisible beat on the corner of Sherbrook and Westminster.

As traffic crawls by, drivers roll down their windows to get a better look at the roller-skate queen of West Broadway, who dances like nobody’s watching, even though everybody is.

Ever since her first skate session nearly two years ago, Cleveland has turned the sidewalk into an impromptu studio for freestyle jam-skating, listening to I Like to Move It, a personalized four-hour playlist starring Dua Lipa, Kesha, Lizzo, Weezer and A Tribe Called Quest. Can she kick it? Yes, she can.

“Skating pings all the perfect spots in my brain,” she said on Nov. 23 as the winter’s first modest snowfall dusted her wheels. “It’s absolutely joyful.”

Normally, the reception from passersby is equally happy. But last year, the skater — who also practises in her apartment with her downstairs neighbour’s permission — got a larger audience when a local viral video page shared a clip of her dancing to its 200,000 Instagram followers.

Nobody from the site asked her permission, and Cleveland quickly broke the first rule of healthy online consumption: never read the comments.

She was disappointed to find anonymous accounts and complete strangers mocking her hobby, her physical appearance and even her technique. The unexpected critiques stung.

But despite the trolls, she continued to dance outside, she told the Free Press in November, getting an hour’s worth of practice before seeing drag performer Thorgy Thor take the stage with the Winnipeg Symphony Orchestra.

“I just really love the sense of freedom I have when I’m on my skates dancing,” she says.

“It’s the perfect combination of fun and silly and challenging. It’s for me. I do it for me. So much of my wellness is found in what skating gives me. Stopping was never a thought.”

Now that the sidewalks are too ridgy and glacial, Cleveland has moved her sessions indoors, clearing out a room in her apartment as a dedicated practice space for what’s become an integral component of her mental and physical wellness.

“I’m lucky my downstairs neighbour isn’t opposed to this, goodness,” she says. “He very easily could be. I reached out to ask if a lot of noise was coming from my place, but he denied any concerns and was really nice.

“I try to be mindful of the hour of day and the length of time I’m banging around for,” she says. “So far, so good.”

Encouraged to continue practising despite the trolls, Cleveland bought herself a sweet new pair of Chaya Melrose Premium Maple Syrup Roller Skates, a set of her favourite toe-stoppers, some fresh wheels and a new set of laces to tie it all together.

She’ll debut those on the sidewalk once the snow melts.

-Ben Waldman