Larry Riddle Spent 3 Years Running From the Law on the Appalachian Trail. Now, He's Giving Back.

Larry “Wanderer” Riddle was rounding out a 2003 work-stay at Bear’s Den Lodge & Hostel when news of Hurricane Isabel tore through the guest-hikers. The storm was set to slash across central Virginia and whip the Blue Ridge Mountains with upward of 20 inches of rain and 60-plus-mph winds. The Appalachian Trail Conservancy (ATC) urged trekkers to beeline for shelter in the nearest town.

“Everybody was getting the hell out of Dodge and begging me to follow suit,” says Riddle, who’s now 65 and owns Crazy Larry’s Hostel (now called Tow’s Place) in Damascus, VA. He launched the business in the late aughts and has a penchant for telling wild stories that seem ripped from the pages of a Bukowski novel. That, plus one of the AT’s most well-stocked donation hiker boxes, have made it a legendary stopover for upward of 1,000 trekkers per year.

But in the Bear’s Den Hostel in 2003, “what those other hikers didn’t know was that I didn’t give a shit what happened to me back then,” says Riddle. He’d been on the AT for three years running from law enforcement after skipping town on parole with a hefty prison sentence hanging over his head. That September, he planned “to hike down to McAfee Knob and take a headfirst dive into oblivion.”

Riddle donned his rain gear and slipped onto the trail while the others packed. He walked south through the evening and spent the night trying to cheer up a pair of worried hikers in the Sam Moore Shelter. The two left the next morning and implored Riddle to join them. Again, he declined.

The weather worsened as the day went on. The sound of the wind-beaten rain was pierced by truncated ringtones as he wove in and out of cell service. Riddle finally answered and was startled to hear his estranged father spluttering about emergency conditions and a rescue.

“He’d talked to the ATC and was trying to figure out where I was,” says Riddle. “But I’d been on the trail during blizzards where it was negative 20 degrees out, so I told him this wasn’t anything particularly crazy and hung up.”

Still, the going was slow and Riddle opted to make camp at Rod Hollow Shelter. He fixed his sleeping bag, mused about the storm in the register, then lost himself in a book and fell asleep. Sometime after midnight, a gust of wind flung him, sleeping-bag-enwrapped, against the log wall. The impact stole his breath and blurred his vision.

“Trees were snapping and falling down everywhere,” says Riddle. Then it struck him: He still wanted to die.

“I scrambled up and tried to throw myself out into the storm—” but a big oak crashed across the entryway, trapping him inside.

“Anger took over,” Riddle continues. “I screamed at God and the trail, ‘I hate how I’ve lived. If you won’t let me die then at least let me change and have a decent damned life!’”

At some point Riddle passed out. He awoke in daylight to a soft downpour, blinked around at the damage—and knew that his time hiding out on the AT had reached its denouement.

“I understood that my time on the trail had introduced me to a wonderful and accepting community where I felt at home for the first time in my life,” Riddle says. “It had shown me how to be at peace with what I’d done and who I am.”

Riddle was ready to hike back to North Carolina and face his past.

When I ask Riddle how his flight from police began, he fans his palms at the air and shrugs, “I started running away from things when I was a kid and couldn’t quit until after that night on the AT.” Riddle’s childhood in an Army family was punctuated by his father’s deployments to Vietnam, constant moves to new bases, and conversations with a sickly and manipulative live-in grandmother.

“She convinced me really early on that my dad hated me,” says Riddle. She said “that was why he went away to fight; that he wanted to die and get away from me.”

When Riddle’s father left for the frontlines, Riddle acted out. He learned to steal and hitchhike by age 13, and used pilfered funds to disappear on adventures that carried him hundreds of miles from Fort Riley, Kansas, to places like St. Louis and Denver. He stole his first car at 17 and drove 200 miles to Kansas City. The stunt landed him in juvenile detention and a kind of bootcamp for troubled boys.

His rebellion only worsened with age.

“I’d go to a new place, make friends, get a decent job, and do pretty good for a while,” says Riddle. But within a few months, “I’d get to feeling like I had to go and cut out like a bat out of hell not caring who I hurt or what I left behind.”

The “abscondences,” as he calls them, spanned two decades and most of the country, often involving stolen cars or property that belonged to a trusting friend, boss, or coworker. A stint in the Navy culminated with time in the brig and a hunger-strike-induced discharge. Kansas City brought bouncer work in an all-night honkytonk and a side hustle selling LSD, Black Beauties, Quaaludes, and other drugs. Then, a broken leg from a brutal street fight led to a job with a family friend turned Colorado Springs house-flipper.

“That’s where I got into hiking,” says Riddle. The man had lost a leg in Vietnam, “and he got pissed about me complaining about my leg hurting and started making me go on all these hikes.”

Riddle loved the way the woods and high-elevation landscape bled into him, banishing anger, guilt, and even identity. A shadow he could never quite catch sight of seemed to evaporate when he was in nature.

“I’d hitchhike somewhere pretty and head into the woods,” Riddle says. But at some point silence overwhelmed him, “and my mind would roar about needing to get back to town and see what’s happening.”

Hunter Thompson-grade benders in random locales across the West commenced. When money ran low, Riddle slept on the streets or pitched his tent in parks. He’d sober up and find Alcoholics Anonymous meetings, “mostly because they were a great place to get work.”

Riddle explored the Grand Tetons and cooked in a diner in West Yellowstone, Montana. He ran a successful Jackson Hole rock shop and spent time in Las Vegas as a habitual gambler. Bad checks landed him in an Idaho jail, while a fistful of stolen casino chips brought 18 months in the Nevada penitentiary. Hanging with the Mongol Brotherhood motorcycle gang inspired a Montana gun-running scheme that yielded months in lockup. He was apprehended in Mexico trying to smuggle undocumented immigrants into the U.S.—and the list goes on.

“I’d ask myself, ‘Why are you doing these things?’” Riddle tells me, his voice addled with emotion. “But I couldn’t find an answer. It’s like my brain would short circuit and—bang!—I’m on a rollercoaster to crazy town.”

The long and miscreant chapter concluded in Bryson City, North Carolina, when Riddle kicked in the door of a chaplain-cum-employer, stole some jewelry, and fled in a work truck. Three months later he was locked in a cell at the Swain County Jail with a 25-year sentence hanging over his head.

Model behavior and pleas from the forgiving chaplain landed Riddle in a transitional work release program in 1999 after about a year. He got a cook job in Bryson City and did maintenance at an assisted living home.

“I was determined not to fuck up,” says Riddle. “I vowed to work hard, keep my head down, and never steal again.”

Then a local produce vendor was murdered in a July 2000 robbery. The town panicked. When Riddle arrived at the seniors’ home, coworkers were gathered menacingly in the lounge. They glared as the team foreman spouted accusations of murder at Riddle citing gang affiliations and a long criminal record.

“I told him in no uncertain words that it wasn’t me, but he called me a liar,” says Riddle. “Then I said, ‘I’m walking out that door and if you follow we’re gonna fight and someone will die.’”

The threat quelled the bluster, but the incident sparked visions of wrongful persecution in Riddle’s mind. He beelined for his apartment, stuffed what he could into two backpacks, slipped into the woods, and picked his way to Smoky Mountains National Park, bound for the Appalachian Trail.

“Back then, I couldn’t have said what made me cut out on the trail like that,” says Riddle. Given his history, it seemed like an improbable escape. But on the other, “I always felt better in the woods, so I guess maybe that’s what I was after.”

Riddle fell in with some straggling NOBOers early on—and discovered his setup was conspicuous.

“I had this huge, external framed backpack stuffed with crap like a 25 by 25 foot tarp, cast iron skillet, and blue-speckled Walmart coffee pot,” he says. A front-slung daypack rounded out the image, “so I was insanely overloaded and looked absolutely ridiculous.”

It didn’t take long for Riddle to discover the magic of the AT. Hikers gifted him new gear and meals. People took him into their homes, offered him odd jobs for cash, and connected him to temp gigs with friends or acquaintances. He struck up a friendship with legendary and now late Bluff Mountain Outfitters founder, Dan Gallagher, who helped him reequip in Hot Springs.

“People were just so good to me out there,” says Riddle. As the miles went on, “I realized that, for the first time in my life, it felt like I fit in somewhere.”

As a self-identified blue-blazer and “hiker trash,” Riddle would walk for a while then hitchhike to a trail community when the urge struck. He’d find cash work and camp in the woods or stay in a hostel or boarding house where credit cards and IDs were unnecessary. He kept his backstory to himself and didn’t stay in one spot for long. Riddle drifted north and south guided by whim, fear, and chance encounters. He made friends with outlier groups like the Humble Hikers From Hell—a hardknock tribe of military veterans, ex-cons, and former bikers who took to the woods to party, trade stories, and heal. Other stretches, he’d hike alone, finding isolation and time to think.

“Sometimes I’d go apeshit and just start grabbing limbs and smashing them against tree trunks screaming my lungs out and absolutely hating myself,” says Riddle. Other times, “I’d walk through a magical stretch of woods or climb to a vista and look out over all that beauty and feel like I was standing side-by-side with God himself.”

The pattern continued for three years. Riddle hiked countless miles and virtually every inch of the trail multiple times. But as time went on, he met more and more hikers and gained notoriety for his wild stories and lengthy residency on the trail. That made it harder to keep his identity a secret.

“Larry had such a big and friendly personality, it was impossible for me to imagine him ever doing anything wrong,” says Phil Bowen, now 76. He befriended Riddle at an AA meeting in Bennington, Vermont, in the early 2000s and invited him to spend the winter in an apartment over his barn. “Larry had a great sense of humor and worked hard,” Bowen continues. “The more he told me about his life on the trail, the more in awe of him I became.”

Bowen helped Riddle get work in a friend’s greasy spoon. The two became close and one night the truth came out.

“When Larry told me what he’d done, it was such a shock I thought he was joking,” says Bowen. Then he realized Riddle was serious. “He wanted very badly to face his past and I said, ‘Look, you can’t run forever—do that and you’ll never be whole.’”

Riddle took Bowen’s advice and set out hiking on the trail for Bryson City around July 2003. At some point, he called his probation officer.

“He goes, ‘I know all about why you left and where you’ve been,’” says Riddle. “‘You’ve been doing good out there and I decided to just let you go. If you’d messed up, we would’ve had the marshals come get you, but you didn’t.’”

The PO said Riddle owed $1,500 in restitution and that if he came down and paid it, he’d be a free man. But as Riddle drew closer, he convinced himself it was a trap. Depression took hold. Memories of prior deeds plagued him. Suicide seemed like the only answer.

“Then Hurricane Isabel brought me a miracle,” says Riddle. “It was like I woke up a different person. I felt confident that I’d changed for the better and had the strength to live a good life.”

Riddle returned to Bryson City in late 2003 and spent 14 months in jail because he didn’t have money to pay restitution. He emerged with a clean legal slate and conscience, and set out for Damascus as “this place has called to me ever since the first time I passed through.”

Riddle had no idea what should come next, but “the AT had saved my life and I knew I wanted to devote myself to that community,” he says.

Riddle found lodging with friends and work doing everything from carpentry to cooking. Integration into the community brought an offer for a cheap downtown rental home about a half-mile from the AT in 2006. Riddle launched a weekend flea market and let trekkers crash in a spare bedroom or pitch tents in his yard. Word spread and Crazy Larry’s officially opened in 2012. He rebranded under the moniker Tow’s Place about a decade later because “people see the word ‘Crazy’ and think of a party spot, which created some problems for me now and then.”

But overall? Riddle describes the hostel business as something of a calling.

“A lot of people that pass through Larry’s place are in a transitional moment in their life,” says longtime Damascus resident and instrument maker, John Dancer. Some hikers use the journey as a rite of passage from college to career; others hope to overcome the horrors of war or a bad marriage; others celebrate retirement by pursuing a lifelong dream. Still others hike as a means of grappling with past decisions—something nobody understands better than Riddle.

“I’ve known Larry for nearly 20 years and I think his greatest attribute is how he’ll always take the time to listen to a person’s story and offer whatever advice he can,” says Dancer. “He’s curious about who they are, where they’re from, and what made them want to hike the AT. Holding that space so that people can express themselves openly and honestly without fear of judgement can be really powerful.”

Health problems and a 2024 heart attack have forced Riddle to scale back operations, but he doubts he’ll ever fully shut his doors.

“I owe the AT an immense debt,” he says. “My time on the trail gave me a second chance at life and I intend to go on paying that forward until the moment I finally run out of breath.”