Dianne Whelan was hoping to make some friends during her trek of the Trans Canada Trail, but sadly, one was killed by a bear and another friend drowned.
Such is life along the 14,900-mile route—the longest trail network in the world—which stretches from the Atlantic to the Arctic to the Pacific Oceans. Most of us consider the 125-hour cutoff for the Cocodona 250 an impossibly long time. It took Whelan six years to reach the finish line.
The Canadian adventurist originally thought her journey would take 500 days, but she was off by about four and a half years.
What struck me most profoundly when speaking with Whelan was how well put together she seemed.
“After the bear incident I got a shotgun,” she told me. “I only had to use it once, and it was just a warning shot. No biggie,” said Whelan.
Dianne talked about the encounter with a casual nonchalance. As she did about the time miscalculation.
“I sold all my stuff before departing, so I wasn’t worried about paying the bills. And I wasn’t lonely out on the trail by myself. Life became simpler. What mattered most was the direction of the wind, the air temperature, the humidity. Many people fear nature, but not me. I love nature. I didn’t mind being out there for so long at all.”
When probed deeper about the rather tremendous scheduling oversight, her response was sober and rational.
“I started out with a plan to cover 50 kilometers a day. After three days of killing myself, I put the plan away. After ten days, I burned the plan at the campfire. Life doesn’t always go as planned.”

Photo courtesy Dianne Whelan
Were there times when she wanted to quit? Surprisingly, not so many. It wasn’t like she was out there relentlessly pushing ahead to be first to complete the world’s longest trail. Forging the Trans Canadian Trail became more of a way of life for her. While some people sit in an office for six years filing paperwork, Dianne Whelan traversed the longest trail in the world. Her adventure makes one ponder how most people spend their lives.
Did she ever feel vulnerable to others, especially as a solo female?
“I’ll be honest, I did have concerns. After all, there was no way to put a lock on my tent door. However, what I experienced was just the opposite. I was helped by literally hundreds of complete strangers. If you watch the news, you think the world is overrun by psychopaths. This wasn’t the case at all for me. I witnessed the best of humankind.”
What about cravings? Nachos and a margarita?
“Ha!” she laughed. “I did indulge in the periodic piece of chocolate, and I delighted in a cold soda on the few occasions I had access. But mostly it was just trail gorp.”
Then she added with a spark of enthusiasm, “Except during berry season. Then it was trail gorp with berries.”
What about the ending? I’ve personally been on a few extended expeditions myself (for months, not years). The finish is not always the glorious celebration people envision. In fact, perhaps the most disconcerting element of being “out there” is coming back. Reintegration to everyday society can be jarring, life can feel overwhelming, intense and lonely. One can only imagine the feelings of returning to “normal” life after being on a wilderness trail for six years.
“I’m not sure I’ve adjusted,” she says. “I’m not sure I ever will. An experience like this is transformative and nothing is ever quite the same.”
“Adventure is just bad planning,” polar explorer Roald Amundsen once quipped. Whelan’s six-year odyssey was undoubtedly partially a bit of imperfect planning. Though if everything had gone according to script, the adventure would have been far less epic. Not only was she forced to learn new survival skills, but she was also confronted with the mental reckoning that if she were to succeed in the undertaking, additional years—not months—would be required. Sometimes the most challenging adventure is within.
When asked if she felt remorse about the four and a half additional years on the trails, the question seemed puzzling.
“That was the greatest adventure of my life,” she mused. “Why would I want it to end early?”
Her reaction made me realize it was my question that made little sense, not her answer. We only get one crack at life, why shouldn’t it be a grand adventure? Whelan reminded me there’s no reason it shouldn’t be.