Homestead grad closes in on the Triple Crown of Hiking

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While many college students go straight to work after graduating, Los Altos native Tom Gabrielson chose a different path – one that has included thousands of miles of some of America’s toughest trails.

The University of Michigan alumnus is two-thirds of the way to his goal of completing what’s known as the Triple Crown of Hiking. Earlier this month, he finished hiking the Continental Divide Trail (3,100 miles), which followed his completion of the Pacific Crest Trail (2,653 miles) in 2022. All that’s left is the Appalachian Trail (2,198 miles), which Gabrielson said he plans to hike “in the coming years.”

“I’ve been hiking with my family since I could walk,” he said. “I remember seeing Appalachian Trail hikers in New Hampshire as a kid, and I thought, ‘I want to do that someday.’”

But first, the Homestead High School graduate needs time to recover from his five-month hike of the Continental Divide Trail, which runs from the U.S. border near Chihuahua, Mexico, to Alberta, Canada.

“On the Continental Divide Trail, there are parts where you feel like a pioneer – (it’s) just you, the trail and miles of wilderness,” Gabrielson said. “In some stretches, I wouldn’t see another person for days.”

Despite the grueling 20-plus-mile days, Gabrielson found the experience transformative.

“Hiking these trails makes you question what you want out of life,” he said. “For me, it’s about chasing goals that are my own – not ones set by others.”

Growing up in Los Altos, Gabrielson was active in Boy Scouts of America. As a member of Troop 33, Gabrielson said he improved his backpacking skills and developed a love for the outdoors. 

That love and those skills surely helped him during the nearly 6,000 miles of trails he conquered on his Triple Crown quest. 

His mom, Joyce Baron, couldn’t be prouder of her son’s accomplishments.

“He is living his best life. As a parent, I could ask for nothing more,” she said. “He decided to do the (Pacific Crest Trail) after COVID, right after graduating from University of Michigan (in 2021), and I just thought, ‘I think it’s great.’”

Despite the challenges and risks, Baron said she and her husband Carl Gabrielson thought it was important for their son to take control of his life.

“If we had said no or told him all the things that could go wrong, honestly, I don’t feel like it would be right. It’s his life,” she said. “You learn more from your mistakes than anything else, and I think he would have always regretted not doing it when he wanted to.”

Tom’s parents said it was difficult to imagine their son alone in the wilderness.

“Anybody who does any of these hikes, they end up having to hitchhike a lot, which is kind of scary as a parent,” Carl said. “But he meets very helpful, very friendly people who care about hikers and take care of them.”

Graduating amid the pandemic, Tom initially considered entering a Ph.D. program but said he felt uncertain about committing to an academic pursuit that didn’t excite him. His time on the trail offered clarity and a new perspective on life’s possibilities.

“Most people think you have to follow a certain path to find success,” he said. “But there are people out here with no fancy jobs who are living incredible lives and exploring the world.”

Tom noted that his time on the trails gave him a new perspective on success and fulfillment. 

“The most meaningful thing about doing these individual trails is the goal that I’ve set for myself,” he said. “I feel like even though someone else made the trail, it’s me fulfilling my own personal goals, which feels more fulfilling and meaningful.”

Along with his goal of completing the Triple Crown of Hiking, Tom said he is also intrigued by other long-distance treks, including the Arizona Trail and the Hayduke Trail, a challenging 800-mile route through Utah’s national parks.

But for now, he is taking things one step at a time.

“If there’s something you want to do, whether it’s hiking or another dream, take the plunge,” he said. “Life doesn’t have to follow a script.”

For those considering a similar journey, Tom recommends preparation and patience. He said a shorter solo backpacking trip should come before thru-hiking, adding that it’s important to give oneself time to settle into trail life before taking on those long-distance treks.

“Expect it to be overwhelming at first,” he said. “But if you stick it out, you’ll find your rhythm. The first few weeks are the toughest, but once you’re in the groove, it’s an experience unlike any other.”

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