Feeling the Wind Again: How Winchester Is Pedaling Into the Cycling Without Age Movement

cycling without age POD

Sometimes the best ideas arrive quietly — through a YouTube video late at night, or a keynote speaker at a conference in Norfolk. For a small but passionate group of Winchester locals, one such idea has grown into a full-fledged movement that is already bringing joy, connection, and fresh air to seniors across the Shenandoah Valley.

In a recent episode of The Valley Today, host Janet Michael sits down with three of the people making it happen. Click here to listen.

A Global Idea Finds a Local Champion

Steve Policastro first encountered Cycling Without Age in 2023 through a YouTube video, and the concept stopped him in his tracks. Founded in 2012 by Ole Kassow in Copenhagen, Denmark, the nonprofit organization operates on a beautifully simple premise: volunteers pilot specially designed three-wheeled electric bicycles — called trishaws — while seniors ride along as passengers, free to enjoy the scenery, feel the breeze, and chat with whoever is beside them.

“As soon as I saw it, I knew that’s what I wanted to do,” Steve tells Janet. “I didn’t know how I was going to do it or when it would happen, but it really touched me.”

For nearly two years, Steve talks about Cycling Without Age to anyone who would listen. Then, through a fortunate connection, he meets Teresa Barton, Wellness Manager at Shenandoah Valley Westminster Canterbury — and everything clicks into place.

The Perfect Partnership

Meanwhile, Jeannie Shiley, President and CEO of Westminster Canterbury, had already caught the Cycling Without Age bug herself. At the Leading Age Virginia conference in Norfolk, she and her team watch a film about the program — and were moved to tears. Before the keynote was even over, her team was already talking about getting not one, but two trishaws.

“We were super, super excited,” Jeannie recalls. When Teresa later connects with Steve, Jeannie immediately recognizes the alignment. “We were trying to get it off the ground here at Westminster Canterbury. Steve’s trying to get a chapter here in Winchester. It was just perfect timing for both sides.”

Westminster Canterbury’s foundation swiftly agrees to fund the community’s first trishaw. Unlike many chapters around the country that spend years fundraising just to get started, Winchester’s chapter has its bike within months of that first meeting — a fact that still amazes Steve.

Built on Five Principles

Cycling Without Age is far more than a feel-good activity. As Steve explains, the organization’s global network of over 3,500 chapters — spanning more than 40 countries and six thousand bikes — is united by five core principles that guide every ride.

Generosity sits at the foundation. Every ride is free, every pilot is a volunteer, and established chapters actively help new ones get started. Slowness is equally essential — these rides are deliberately unhurried, designed to let passengers absorb their surroundings and strike up conversations along the way. Storytelling encourages pilots to draw out memories and life experiences from the people they carry. Relationships naturally follow, as bonds form between volunteers and riders. And finally, without age captures the spirit of the entire endeavor: aging is universal, but it doesn’t mean stopping.

Rolling Out in Winchester

Winchester’s chapter officially launched in style — literally. The community’s new trishaw made its public debut in the Apple Blossom Parade, banner and residents in tow, generating excitement across the city before a single scheduled ride had taken place.

Shortly after, Westminster Canterbury holds its official on-campus launch. The weather was drizzly, but that didn’t stop eight residents from climbing aboard for rides through the campus grounds, which include the main building, cottages, and surrounding villas. The smiles, according to everyone present, said it all.

“One resident walked out and looked at it and says, ‘I’m not sure I can pedal that thing,'” Jeannie laughs. “And I said, ‘The good news is — you don’t have to.'”

For now, rides take place on weekends in two-hour blocks, offered in 15-to-20-minute increments so that multiple residents can participate each session. As the program grows, the team plans to expand beyond campus — eventually taking riders to Winchester’s downtown walking mall, museum trails, and other beloved local destinations.

A Community Invitation

The vision, however, extends well beyond Westminster Canterbury’s gates. Steve envisions trishaws carrying passengers at Jim Barnett Park, outside Winchester House, and throughout the city’s growing network of bike-friendly streets. To make that happen, he is actively fundraising for a second trishaw through Cycling Without Age Winchester, a registered 501(c)(3) nonprofit.

The chapter currently has 15 trained pilots — drawn largely from BikeWalk Winchester and the Winchester Wheelmen — but is always looking for more. Importantly, you don’t need to be an athlete to participate. If you can ride a bike, you can be a pilot.

“It’s about making people happy,” Steve says simply. “And I can’t think of anything better to make them happy than a bike ride.”

Get Involved

Whether you want to volunteer as a pilot, contribute to the second trishaw fund, or simply spread the word, there are plenty of ways to support Cycling Without Age Winchester.

And to hear the full, heartwarming conversation with Steve, Jeannie, and Teresa — including what it actually feels like to glide through the streets in a trishaw — listen to the complete episode of The Valley Today here: https://thevalleytodaypodcast.com/cycling-without-age-bringing-winchester-along-for-the-ride

It just might inspire you to take a ride.