In this episode of Into the Hearts of Canada, Matt Leedham sits down with filmmaker, writer and adventurer Dianne Whelan who created 500 Days in the Wild. What began as a solo crossing of the Trans Canada Trail (24,000km across land and water) became a six-year pilgrimage of healing and reconnection from Newfoundland to the Arctic and, finally, the Pacific.
Into the Hearts of Canada is an engaging 10-part series that explores the people, places, and powerful ideas shaping the future of travel through a Canadian lens.
From Indigenous knowledge-keepers and local changemakers to iconic landscapes and regenerative tourism pioneers, each episode offers an intimate conversation with the people reimagining what travel can be. Whether you’re a curious wanderer or a travel professional seeking fresh insights, this podcast invites you to see Canada with new eyes and an open heart.
Episode 7: 500 Days in the Wild — Dianne Whelan’s sacred journey across Canada
Can you imagine embarking on a solo journey that ultimately takes six years to complete?
A documentary filmmaker known for This Land (Arctic Canada) and 40 Days at Base Camp (Everest), Dianne set off on July 1, 2015, from St. John’s, Newfoundland, and finished in Victoria, BC, on August 1, 2021, weaving together 487 land and water trails into one continuous line.
“I didn’t make a list of why I couldn’t go. I made a list of what I had. And I made a plan,” she says.
Remarkably, she filmed almost the entire journey herself. The end product is the documentary and spectacular Canada showcase, “500 Days in the Wild,” which is set to premiere on screens in Australia in early 2026. It’s also available to watch on Air Canada flights now.
Whelan also appeared at the recent Destination Canada’s Focus Canada week as a guest of Adventure World, sharing her incredible story and learnings at several travel trade events in Sydney.
Episode Top Takeaways
From heartbreak to horizon: Turning 50, navigating the end of a 13-year marriage and the loss of her 16-year-old dog, Dianne traded her home for the horizon with a 40-year-old bike, a battered backpack and a camera.
“When you love what you do, the pain has a purpose.”
The feather that shaped the path: Before leaving, an elder in Haida Gwaii (Vern Williams) gifted Dianne his eagle feather. Caring for it daily transformed the expedition into a journey of reconciliation. She spent time in over 15 Indigenous communities, listening, learning, and participating in ceremonies.
“Our lives are shaped by what we carry in our hearts.”
Slow, meaningful travel, not conquest: Six years. 800 hours of footage. Paddling 8,000km of water, snowshoeing winter trails, biking old rail lines, hiking ancient paths.
“It’s not about the fastest or easiest way — it’s about the most meaningful way.”
Encounters of courage & kindness: Near the Arctic, tragedy struck others on the same waters, serving as stark reminders of fragility and luck. Dianne finished with gratitude, not ego:
“Every man I met treated me with respect. It was healing.”
Canada’s deeper story: Across the country, Dianne witnessed a rebirth in Indigenous communities, as language, songs, and ceremonies experienced a resurgence.
“You can be proud of your country and still honour the ancestry that anchors it, like a tree whose deepest roots strengthen its branches.”
Logistics on a shoestring: Indie-filmmaker resupplies, borrowed canoes, solar charging on the move, and backing up footage to twin drives at trailheads. Plus a fair share of mishaps:
“I went through five tents in the first few months… one literally blew away.”
Show Notes
- Find out more about 500 Days in the Wild (film & screenings) here
- Explore the Trans Canada Trail here
- Subscribe to Into The Hearts of Canada Podcast here
- Find your local Canada Specialist Travel Advisor here
- Travel Advisors: Join the Canada Specialist Program here
Catch up on past episodes
Into the Hearts of Canada is presented in partnership with Destination Canada.
