CALEDONIA—From sea to shining sea, Caleb Leary is pedalling across Canada in honour of animals, adventure, and a song that would not let go.
The 28-year-old Caledonia resident left Tofino, British Columbia on May 21, 2026, beginning a coast-to-coast cycling journey he calls the Courage Canada Crossing.
His planned route stretches from Vancouver Island to Cape Spear, Newfoundland, with stops at Canadian landmarks, Tragically Hip-related sites, and animal sanctuaries along the way.
Leary said the idea grew from three things close to him: his Canadian heritage, animals, and The Tragically Hip.
“I have to say that my biggest inspiration came from The Tragically Hip, and Gord Downie in particular,” he said. “The Hip have been my favourite band for many years. Their music really captures the Canadian identity and so many of the stories that have shaped this country.”
Leary said Downie’s later work with the Gord Downie & Chanie Wenjack Fund pushed him to think about giving back.
“I thought, ‘What could I do that would combine my love for The Hip, my love of animals, and my love of adventure?’ And that’s kind of what led me to choose this bicycling journey,” he said.
The ride is raising money and awareness for animal shelters, sanctuaries, and rehabilitation centres across Canada. Leary, who volunteers with the Hamilton/Burlington SPCA, said he wanted to encourage people to look beyond larger organizations and consider smaller sanctuaries doing important work locally.
Through his GoFundMe page, Leary wrote that every dollar donated to the campaign will go to Canadian animal sanctuaries in need. He also encouraged supporters to use an interactive map from PEACE Canada to find and donate directly to sanctuaries close to them.
“Just to be especially clear, none of the money donated will go toward myself or funding my journey – every penny will be donated,” Leary wrote.
Leary does not yet have a final list of sanctuaries that will receive funds. He has already visited some on his route, including a llama sanctuary in Tappen, BC. He also mentioned sanctuaries he has in mind to support, such as Hobbitstee Wildlife Refuge in Haldimand.
Chantal Theijn, founder of Hobbitstee, is grateful for any support received.
“Fundraisers such as these provide vital money for the work we do and we appreciate them very much,” she said.
Leary’s ride is not supported by a team travelling with him. Travelling alone with his bike, he has met many supportive people so far.
“I’ve met some friendly folks along the way who are doing similar journeys, and they’ve passed on some knowledge,” he said. “That’s kind of the best part of the entire trip, right? It’s just the people that you meet along the way.”
The challenge has been especially steep because Leary started with no cycling background.
“I have absolutely no experience,” he said. “I didn’t even own a bicycle until a few months before I set out on this trip, so it’s all been new to me.”
He said that has meant learning not only how to ride long distances, but also how to understand his bike and fix problems on the road.
One of those problems came in Thunder Bay, where Leary had to replace his back rim after a spoke pushed through and destroyed it.
“That was a bit of a setback, but overall, it’s been pretty good,” he said.
Leary said weather has been one of the biggest challenges, with days often shaped by what conditions allow.
Rain has been frequent, though not enough to stop him. Safety on highways requires constant attention, especially on northern highways where the shoulder can narrow or disappear as transports pass.
“There’s an element of danger to riding a bike alongside highways,” he said. “I have to hold my breath sometimes as the trucks go behind me.”
Wildlife has been another factor. Leary has seen black bears nearby the road, keeping bear spray at the ready in many areas.
“You just proceed with caution and try not to panic, which is easier said than done when you’re staring a big bear in the eyes,” he said.
Despite the obstacles, Leary said support from donors, family, and friends has helped keep him moving. He thanked his parents, Rob and Lisa, and his girlfriend, Kelly, who has helped with social media for the ride.
“I couldn’t do it without her,” he said.
He said the amount raised so far and the response from people following the journey have been powerful motivators.
“It’s really about the people and the cause that help motivate me to keep going,” he added.
The ride has also given him a close look at Canada’s landscape. Leary said travelling through the Rocky Mountains was one of the most memorable parts of the trip, even with the difficulty of climbing summits by bike.
“You stop and you look around and you feel so small when you’re on the road next to these enormous mountains,” he said.
Every day has offered something different.
“Each part of Canada has its own beauty,” said Leary. “Even the Prairies – there might not be as much there, but there’s a certain element of beauty in the vastness of the fields.”
The route was inspired by “Silver Jet,” a song from The Tragically Hip album In Violet Light. Leary said the song’s final line references Clayoquot Sound (near Tofino) and Cape Spear, giving him the start and end points for the ride.
“That line inspired me,” he said. “It kind of brought everything together of this adventure, and what I could do to help raise money for this thing that I’m so passionate about.”
Leary hopes to finish before August 15, when he must attend a friend’s wedding. He is leaving a career in kinesiology and ergonomics after five years, with plans to start school in September to become an MRI technician.
Leary said he hopes the Courage Canada Crossing encourages others to act on their own passions.
“Sometimes, you just gotta’ go out and do the things that you’re passionate about doing,” he said. “I hope that if anyone is reading the article or knows about my story, that it maybe would somehow inspire them to take up something that they’re passionate about in their own life.”
As of June 29, Leary has raised about $1,300. To donate, visit gofundme.com/f/courage-canada-crossing.
