The New Wisdom: 6 Long-Trail Legends Share Hard-Won Advice

With 140,000 miles (and counting) behind them, they’ve got ideas that work.

Every year, thousands of hikers set off on thru-hikes. While many quit before they reach the trail’s end, about a quarter keep on walking to a successful completion. A much smaller percentage—like these six hikers—never stop.

By walking full-time anywhere from five to twelve months out of the year, every year, these “trail celebrities” make their way into the lore of long trails, as well as into one another’s lives. There are around 25 or so true full-time hikers in the U.S. They all know each other, and most have known each other for years.

On the trail, meeting someone who’s shared the same hikes and the same challenges comes across with the same strength of familiarity as meeting someone with a shared hometown. Friendships form fast and deep, and though the long distance hiking community is disparate and dynamic, spread all over the world, they’re always there for each other.

Here are some stories and lessons from that pool of shared wisdom.

Freebird (Dave Osborn)

On the Trails Since: 1996
Distance Hiked: Over 30,000 miles

Photo courtesy of Freebird

While competing as a professional windsurfer in Japan, Freebird had a realization that eventually changed his life. When he looked to the 150,000-person audience, he saw Japanese models tossing cigarettes, party favors from the competition’s sponsor, into the eager crowd like confetti. He was horrified.

“I didn’t want to be a marketing tool for selling cigarettes,” he said. So he quit his career as a globetrotting pro and became another kind of athlete, hopping on the Appalachian Trail in 1996. One year later, he bought a one-way ticket to California and found a San Diego State student to drop him off at the Mexican border with butterflies in his stomach.

One of the first mistakes he made was bringing a hammock, which he carried for miles without ever setting up. “When you’re thru-hiking, you can’t help but notice how things that are considered luxuries quickly become a burden,” he says.

Flexibility is key. Storms, fires, trail reroutes, and injuries will happen, but “don’t allow the fear of not finishing compromise your thru-hike.”

He fell in love with the tight-knit trail community, a barter society where hikers joke that cash is “fit for legal tinder” and you can walk freely without having your lifestyle questioned or worrying about crossing into private property.

“When you’re living in a house, you have nice neighbors but you hardly ever see them,” he says. In contrast, he found a true community on the trail, where common interest and common suffering throw together people from radically diverse backgrounds. “It’s misfits and exiles, but it’s a real family who cares about each other,” Freebird says.

Freebird has now hiked more than 30,000 miles. His resume includes thru-hikes of the PCT and AT (three of each), CDT, Te Araroa Trail, Hayduke Trail, Grand Enchantment, Florida Trail, Lost Coast Trail, West Coast Trail, and Long Trail, to name a few.

Strange but true: “You’ll probably sleep in a bathroom and eat out of a dumpster before your thru-hike is over.” It’s part of the journey.

His advice: Know that storms, fires, trail reroutes, and injuries will happen; stay flexible. “Rigid plans and schedules don’t work well with thru-hikes because there are so many unexpected variables,” he says. “Enjoy every day, and don’t allow the fear of not finishing compromise your thru-hike.”

Oh, and when Billy Goat predicts you’re going to sleep in a bathroom and eat out of a dumpster before your thru-hike is over, don’t tell him he’s wrong unless you like eating your words later.

Billy Goat (George Woodward)

On the Trails Since: 1988
Distance Hiked: Over 47,700 miles

Billy Goat | Photo courtesy of NPS, Deby Dixon, Flickr

“If thru-hikers are some kind of dysfunctional family or tribe, Billy Goat is the chief,” says Freebird, who met the legend himself on March 19, 1996, the last day Billy Goat ever shaved. “To me, he is the last American mountain man. The rest of us seem like we’re visiting the wilderness. Billy Goat seems like he belongs.”

Billy Goat’s response is characteristically pragmatic. “Oh, I don’t know. I’m not a movie star. I’m not a baseball player. I just walk. That’s all I do.”

And it’s all he’s been doing for the last 28 years since he retired from railroad work at age 50. He’s now hiked over 47,700 miles. “It doesn’t register with people until I tell them it’s as many miles as their car has. Then they’re surprised. But the difference is their car goes 50 to 60 miles per hour and I don’t,” he laughs.

Your #1 priority? The trail. “You don’t need to take a week off and go to San Francisco or South Lake Tahoe for a music concert. If you want to go to a music concert, why are you hiking the PCT?”

Billy Goat’s a no-nonsense, no-frills kind of guy, but when he talks, even over the phone, it sounds like he has a twinkle in his eye. And when he speaks, people listen. His beard is the stuff of trail mythology, and hikers frequently come up to him, asking if he’s John Muir and whether they can take a picture with him. Nowadays, Freebird says, the 78-year-old just says yes and smiles for the camera.

“I do think I’m quite an encouragement to older men who think it’s too late for them,” says Billy Goat. “As you get older, with each year that goes by, if you postpone being physically active, it’s harder and harder to become fit,” he says, emphasizing that there’s no time like the present to walk out your door and go for a hike.

“I make it a goal to hike someplace every month of the year, even if it’s just one day. I don’t want a month to go by if I haven’t hiked someplace.”

His advice for other hikers: “Take it easy! You’re not going to get to Canada today. Maybe not even tomorrow.”

Avoid meals composed entirely of Snickers bars.

He says people rush things too often, focusing on the start and end of the trail when everything that will happen to you will happen somewhere in between. “Stay steady and regular and on the gentle side,” he says. “And you don’t need to take a week off and go to San Francisco or South Lake Tahoe for a music concert. If you want to go to a music concert, why are you hiking the PCT?”

He also recommends new hikers learn how to use their camp stove before they set foot on the trail. And avoid meals composed entirely of Snickers bars. Complex carbohydrates will serve you better in the long run, he says, recommending his own fuel: rehydrated black beans, buckwheat groats, and vegetables. “Beans have go power.”

Not A Chance (Amanda Timeoni)

On the Trails Since: 2009
Distance Hiked: Over 13,500 miles

Photo courtesy of Not a Chance

Not A Chance has walked over 13,500 miles—and against plenty of odds. Though she said her trail name was first bestowed upon her by “creepy dudes,” it quickly came to describe her (un)likelihood of finishing her first PCT hike in 2009.

“I was pretty bad at thru-hiking my first year. But stubborn enough!” she says.

Stay healthy. Bring a multivitamin.

Chance was successful that first year and is still riding that wave today. Now 32, she works on farms and in pizza parlors during her six- to seven-month off-season to fund her travel and hiking ventures.

The thing that keeps her going?

“Oh, man. I love living outside and waking up to birdsong. It’s really simple, and it gets you back to your primal self, and that’s when I’m happiest. I have a lot of anxiety in the real world, and the trail is one of those places that teaches me a lot about myself, about the world, and about people,” she says. From the trail, she’s learned not sweat the small stuff and to have faith in humanity.

“You see a lot of selfless giving on the trail,” she says. “And every time you’re like, ‘Oh man, I’ve got to do something good to make up for this.’” It’s an ongoing cycle of random acts of kindness.

Her love of solitude has driven her toward less-populated trails as years have passed, and a bit of solo hiking is something she’d recommend to anyone. “Hike alone. Nature vibrates louder,” she says.

Oh, and one more piece of advice for folks setting out on their first long hikes: “Bring a multivitamin!”

Wired (Erin Saver)

On the Trails Since: 2011
Distance Hiked: 12,500

Photo Courtesy of Wired

It took a little bit of cultural shock to nudge Wired into the thru-hiking life.

“I was from Chicago, and I had those midwest values. You work really hard, you retire, and then you do things,” she says. But when she moved to Portland at age 31, she realized you didn’t have to wait for retirement to have an adventure.

Though she runs a successful blog, Wired says that her thru-hike funding comes entirely from working long hours as a nanny and substitute teacher during her off-season.

On her blog, she offers stories, trip logistics, and advice to prospective hikers for free. For her, it’s a way to give back to the long distance hiking community, to whom she owes her own success. Among thru-hikers there exists an informal mentorship system. A new hiker will learn the tricks of the trade from a veteran, and in turn, will pass that knowledge along to any upstart earnest enough to ask.

Tweeting or ‘graming your hike? Reflect the whole experience on social media—the pain as well as the pleasure.

In the past two or three years, there has been some breakdown in that tradition, Wired says. She’s noticed a number of hikers, most of whom received their tutelage for free, selling what they know through online classes or consultation phone calls with hourly rates.

“I think it’s undermining the closeness of the community and the mentorship tradition. It can make it hard to know who to trust,” she says, having seen friends’ personal maps sold without their permission. Wired adds that she doesn’t disparage the existence of hiking classes—many of which are helpful to those new to the trail—but she does advise hikers to stay mindful of the reasons that brought them the wilderness in the first place and make sure social media doesn’t complicate a way of life that should find its appeal in simplicity.

She also advises newcomers to keep their expectations realistic. Likewise, it’s important for existing hikers to reflect the whole experience of a hike on social media—the pain as well as the pleasure.

“I’ve been on a lot of trails where people quit within the month,” she says. “They see all the pretty photos and they want the wanderlust. They want the dreams, and they don’t want to worry about the pain or the money that goes into it or how tired you always are or the sacrifices you make in other parts of your life.” All of that richness is what makes thru-hiking beautiful, and it all deserves a mention: the joy, the suffering, and the sacrifice alike.

Buck 30 (Brian Tanzman)

On the Trails Since: 2002
Distance Hiked: About 25,000 miles

Photo courtesy of Buck 30

Buck 30, named for the quantity of change he accidentally carried for the entire length of the Appalachian Trail, has now walked the equivalent of the circumference of the earth: about 25,000 miles.

“I truly cannot remember why I went into the managing partner of my office and asked for a six-month leave of absence,” he says. That was in 2002 when he was a 27-year-old accountant. “I wasn’t unhappy. I just wanted to do something.”

Now, Buck 30 works for three months out of the year and hikes for nine. For him, having a place to come back to and a job to throw himself into—the coworkers, the socialization, a little dose of the rat race—that’s a comfort.

You don’t have to give up your desk job to spend a lot of time on the trails. It’s OK to want to return to a nine-to-five. “Balance is important.”

“Balance is important,” he says, and unlike a lot of full-time hikers who feel unanchored and directionless during the off-season, he feels like having community to come back to keeps him grounded. Like Wired, who prefers spending time with non-hiker friends during the winter because it gives her a break from trail talk, Buck 30 acknowledges that it’s nice to have a change of pace.

During the hiking season, he’s often alone. A self-identified introvert, he says the isolation has never bothered him. “I think that’s one of the things that does differentiate people who rack up a lot of miles. It takes a certain type of person to be in their own head for so much time,” he says.

He wouldn’t mind a partner every now and again, but long-term hiking buddies are hard to nail down, and it’s easy to watch a lifetime go by waiting for the right person to be available. “I don’t ever want to let the lack of a partner stop me,” he says.

Buck 30 says that, aside from his first AT thru-hike, his proudest achievement is going after his current lifestyle, as unusual as it may be, and making it work for him. “I don’t have any deep philosophical insights,” he laughs. “I just truly enjoy what I’m doing so I keep doing it.”

Wyoming (Mary Ann Lang)

On the Trails Since: Uknown
Distance Hiked: Who’s counting?

Photo courtesy of Wyoming

When did Wyoming start spending half of every year on the trail? “When I realized it was my home,” she says.

The numerical answer is a little harder. “Heck, it’s hard to say. I’ve been on the road most of my life. I didn’t grow up exactly like you’re supposed to, and walking is very therapeutic.”

Get comfortable with hiking solo. Learning how to stand on your own two feet is part of the lesson of the trail.

She left home in Ohio for Wyoming when she was 18. Now 37, one of her proudest accomplishments is the 1,000-mile Centennial Trail through Idaho, which she completed in 2015. Now she’s eyeing the Hayduke and Great Divide Trails, but she’ll keep coming back to her namesake state. “You look at that scenery, and it gets to your heart,” she says.

Now she works in hospitality during the off-season, cooking and housekeeping at lodges with her husband, who does not hike with her. Instead, she walks in the comfort of her own thoughts and makes friends as she goes. “You meet the most wonderful people, and it’s the people you meet who keep you going,” she says. “Nobody has any facades.”

And one last tip: Learn how to use your stove before you hit the trails.

It’s lonely when paths split again, and there are plenty of tough days. But learning how to stand on your own two feet is part of the lesson of the trail, and oftentimes, the woods and dirt singletrack are companions enough. “I never feel more myself or more at home than when I’m out there,” Wyoming says.