Stunning photos and lessons from six years trekking Canada’s longest trail

In 2015 Dianne (pronounced Dee-Anne) Whelan rented out her house, sold her car, cancelled her monthly bills. Over the next six years and one month she walked and paddled all 27,000 kilometres of the Trans Canada Trail (formerly The Great Trail ), becoming the first person ever to cover all land and water portions.

“It was the most remarkable experience,” says Whelan. “It filled my head and heart with positivity.”

Squiggling through every province and territory, from the Atlantic to the Pacific, northern Alberta to the shores of the Arctic Ocean, it’s the longest trail on earth.

Whelan first heard about the trail when her mother donated money to the fledgling idea in the early 1990s. Her desire to travel the route came to her after making documentaries about trips to Mount Everest and the Arctic.

“I’d been to the highest place on earth and the coldest place on earth,” she remembers. “Documenting the longest trail seemed like a good next project.”

Others have walked the land portions, but Whelan was the first person to also paddle the 7,000 kilometres of the route along rivers and lakes. She did all, but a few hundred kilometres by herself, finishing in Victoria, B.C. on August 1, 2021.

Back home on B.C.’s Sunshine Coast, working on a documentary and book about her journey, Cottage Life caught up to her to find out what she learned along the way.

Lesson #1: It’s a really, really long trail

When I started the project in 2014 I thought, wouldn’t it be great to release the film to coincide with the official opening of the trail in 2017. What a joke. I knew by day 10, when I hadn’t even gone as far as I planned to go in one day, it was going to take a lot longer than 500 days.

Lesson #2: Freedom doesn’t have a schedule

Our society is so numerically focused. We measure everything. Yet many of the most important things in life can’t be measured. I realized on Day 10, if I was going to survive the journey, I had to take off my rabbit suit and put on the tortoise shell. It wasn’t about the fastest, it was about the most meaningful. When I made that switch the trail became my home.

Lesson #3: Respect your elders

They say to know your ancestors you have to walk the land they walked. My dad’s family is from Newfoundland. My mom’s family are Acadian. They’ve been in New Brunswick since the 1600s. That history added a deeper connection. But I’m also a person of settler descent. I wanted to pay my respects to my ancestors and also pay my respects to the original people.

Lesson #4: There’s hope out there

Even in 2015, anxiety was already holding people. It only got worse with the weight of climate change, COVID and all the uncertainty. Despite everything, I came home with a lot of hope and I found it in the Indigenous communities. As I travelled through different First Nation cultures, I found the basic ideas share a common theme: live with nature, not on it. They’re connected by the seven generations thinking. We’d make different decisions if we think beyond four months or even four years to seven generations. We need to come back into sustainability. We need to bring traditional wisdom and science and technology together. Weaving the two will take us from danger to safety.

Lesson #5: Solitude reveals what the mirror cannot

There’s a difference between alone and solitude. Humans are only 0.01 percent of life on earth. Being alone is a chance to connect with the other 99.99 percent. But it is humbling to be a fragile being on the shore of Lake Superior. Something ancient wakes up in your DNA. You feel more connected to everything. You develop a relationship with birds and the water—but I never found love for the ticks and black flies.

Lesson #6: It’s not the craft, it’s the intention

I thought by hiking, paddling and snowshoeing I was travelling “the old way.” But in New Brunswick Grand Chief of the Mi’kmaq Ben Sylliboy told me the “old way” is not how you travel but what you carry in your heart. He told me with every stroke I should say, “Water is sacred.” I changed it to “The earth is sacred” when I was walking. I didn’t do it all the time, but when I was afraid I did. The words of Sylliboy refocused me to commit to the physical environment.

Lesson #7: Canadians are really nice

I never met anyone that wasn’t kind. We give the shadow so much weight. It’s the lead in news stories, plays and TV, but 99 percent of the people I met were kind. The few scary moments I had were allusions. The Indigenous people I met, especially, were so kind and open-hearted.

Lesson #8: The Trans Canada Trail is a gift

The trail connects us all across land and water. It’s what we as Canadians share. And I think that the trail makes it clear that our future is about clean air and water. Not the economy. It’s the things that sustain life that are important. And that’s true for all of us, not just one segment of society.

Lesson #9: Explore your backyard

Even though I’ve lived on the Sunshine Coast a long time I had never paddled up to Smugglers Cove until I did it on the journey. It’s so beautiful here. One of the things I’m most excited about being home is exploring my backyard.

Lesson #10: It takes a country to travel 27,000 kilometres

When I pulled into Victoria at the end of the trail, I was greeted by the daughters of the chief of the Songhees Nation. We followed a traditional protocol: I stayed in my boat and introduced myself before they welcomed me ashore. They looked around the crowd of people and said “we are all one.” I was so grateful for that message. Twenty minutes before I had been thinking about how I couldn’t have done it without the help of hundreds of people.

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This fall, hike part of the Trans Canada Trail: join the Great Canadian Hike 

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