From Fugitive to Hostel Owner: Larry "Wanderer" Riddle’s Unlikely Redemption on the Appalachian Trail

Updated March 2, 2026 12:14PM

Larry "Wanderer" Riddle was nearing the end of a 2003 work-stay at Bear’s Den Lodge & Hostel, a temporary haven for weary travelers, when the ominous news of Hurricane Isabel began to circulate among the guest-hikers. Forecasters predicted a devastating path for the storm, poised to unleash its fury across central Virginia and lash the majestic Blue Ridge Mountains with an onslaught of up to 20 inches of rain and winds exceeding 60 miles per hour. In response to the escalating threat, the Appalachian Trail Conservancy (ATC) issued urgent advisories, imploring trekkers to seek immediate shelter in the nearest available towns.

"Everybody was getting the hell out of Dodge and begging me to follow suit," recalls Riddle, now a seasoned 65-year-old proprietor of Tow’s Place, formerly Crazy Larry’s Hostel, nestled in the picturesque town of Damascus, Virginia. He established this renowned establishment in the late aughts, cultivating a reputation for his captivating, often gritty, narratives that seem to spring directly from the pages of a Charles Bukowski novel. This penchant for storytelling, coupled with one of the Appalachian Trail’s most generously stocked donation hiker boxes, has cemented Tow’s Place as a legendary stopover, welcoming upwards of 1,000 trekkers annually.

However, in the quiet solitude of the Bear’s Den Hostel back in 2003, Riddle harbored a secret that set him apart from the fleeing guests. "What those other hikers didn’t know was that I didn’t give a shit what happened to me back then," he admits, his voice tinged with the weight of past experiences. For three consecutive years, Riddle had been immersed in the rugged embrace of the AT, not as a recreational hiker, but as a fugitive from law enforcement. He had absconded from parole, a substantial prison sentence looming over his head. That September, his grim intention was stark: "to hike down to McAfee Knob and take a headfirst dive into oblivion."

Donning his rain gear, Riddle slipped onto the trail as the other guests frantically packed their belongings. He moved south through the encroaching evening, spending the night at the Sam Moore Shelter, attempting to offer solace to a pair of anxious hikers caught in the escalating storm. The following morning, they departed, imploring Riddle to join them, but he steadfastly declined.

As the day wore on, the weather intensified. The relentless drumming of wind-whipped rain was punctuated by the fragmented chirps of cell phone ringtones as Riddle’s signal flickered in and out of reception. He finally answered a call, only to be startled by the strained voice of his estranged father. His father, visibly agitated, spoke of emergency conditions and the possibility of a rescue operation.

"He’d talked to the ATC and was trying to figure out where I was," Riddle explains. "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." His dismissive response, however, belied the true gravity of his internal struggle.

The going remained arduous, and Riddle decided to make camp at Rod Hollow Shelter. He meticulously secured his sleeping bag, penned his thoughts about the storm in the shelter register, and then lost himself in the pages of a book before succumbing to sleep. Sometime after midnight, a violent gust of wind tore through the shelter, flinging him, still swaddled in his sleeping bag, against the rough-hewn log wall. The impact stole his breath and momentarily blurred his vision.

"Trees were snapping and falling down everywhere," Riddle recounts, the memory vivid. It was in that moment of disarray, amidst the tempest’s fury, that a chilling realization struck him: his desire to end his life remained.

"I scrambled up and tried to throw myself out into the storm—" he begins, but his desperate attempt was thwarted. A colossal oak, uprooted by the gale, crashed across the entryway, effectively trapping him within the confines of the shelter.

"Anger took over," Riddle continues, his voice rising with the remembered emotion. "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 during this internal conflagration, Riddle passed out. He awoke to the soft patter of a downpour as daylight illuminated the scene of destruction. The widespread damage was undeniable, and in that moment, Riddle understood that his prolonged period of evasion on the AT had reached its inevitable conclusion.

"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 reflects. "It had shown me how to be at peace with what I’d done and who I am." With this profound realization, Riddle felt a new resolve; he was ready to hike back towards North Carolina and confront the past he had so desperately tried to outrun.

When asked about the genesis of his lifelong flight from authority, Riddle fans his palms in the air with a characteristic shrug. "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, marked by the transient life of an Army family, was a tapestry woven with his father’s deployments to Vietnam, constant relocations to new military bases, and the pervasive influence of a sickly and manipulative live-in grandmother.

"She convinced me really early on that my dad hated me," says Riddle. He recalls her poisonous whispers: "that was why he went away to fight; that he wanted to die and get away from me." This deeply ingrained familial trauma fueled a rebellious spirit that manifested early and persistently.

As his father prepared for his departure to the front lines, a young Riddle’s behavior escalated. By the age of 13, he had acquired the skills of clandestine acquisition and hitchhiking. He used pilfered funds to embark on clandestine adventures, traveling hundreds of miles from his home at Fort Riley, Kansas, to destinations as diverse as St. Louis and Denver. His rebellious streak culminated at 17 with the theft of his first car, a joyride that carried him 200 miles to Kansas City. This act of defiance landed him in juvenile detention and a rigorous bootcamp for troubled youth.

His pattern of rebellion, however, only intensified with age. "I’d go to a new place, make friends, get a decent job, and do pretty good for a while," Riddle explains. Yet, inevitably, 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."

These self-described "abscondences" spanned two decades and traversed much of the country. His escapades frequently involved the appropriation of vehicles or property belonging to individuals who had placed their trust in him—friends, employers, or coworkers. A period of service in the Navy concluded prematurely with time spent in the brig, followed by a discharge precipitated by a hunger strike. In Kansas City, he found himself working as a bouncer in an all-night honky-tonk, supplementing his income with a clandestine side hustle dealing a variety of illicit substances, including LSD, Black Beauties, and Quaaludes. A brutal street fight resulted in a broken leg, which in turn led him to a job with a family friend who was a house-flipper in Colorado Springs.

"That’s where I got into hiking," says Riddle. The man who offered him employment 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." It was during these forced excursions into nature that Riddle discovered a profound connection to the wilderness. He found that the expansive woods and high-elevation landscapes seemed to absorb his inner turmoil, effectively banishing anger, guilt, and even the very sense of self he struggled to define. A pervasive shadow, elusive and intangible, appeared to dissipate when he was immersed in the natural world.

"I’d hitchhike somewhere pretty and head into the woods," Riddle recalls. However, the profound silence of the wilderness would eventually become overwhelming, and "my mind would roar about needing to get back to town and see what’s happening." This internal conflict would trigger a descent into Hunter S. Thompson-esque binges in disparate locations across the West. When his financial resources dwindled, Riddle resorted to sleeping on the streets or pitching his tent in public parks. In moments of sobriety, he would seek out Alcoholics Anonymous meetings, "mostly because they were a great place to get work."

His restless wanderings led him to explore the majestic peaks of the Grand Tetons and to work as a cook in a diner in West Yellowstone, Montana. He later managed a successful rock shop in Jackson Hole and spent time in Las Vegas, succumbing to the allure of habitual gambling. A trail of bad checks landed him in an Idaho jail, while a handful of stolen casino chips resulted in an 18-month sentence in the Nevada penitentiary. An association with the Mongol Brotherhood motorcycle gang inspired a Montana gun-running scheme that led to several months of incarceration. His transgressions continued, culminating in his apprehension in Mexico while attempting to smuggle undocumented immigrants into the United States—and the list, he admits, goes on.

"I’d ask myself, ‘Why are you doing these things?’" Riddle tells me, his voice thick with a mixture of bewilderment and 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."

This long and miscreant chapter of his life finally reached a critical juncture in Bryson City, North Carolina. Riddle broke into the home of a chaplain who had employed him, stole some jewelry, and fled in a work truck. Three months later, he found himself incarcerated in the Swain County Jail, facing a daunting 25-year prison sentence.

Demonstrating remarkable model behavior and benefiting from the compassionate intercession of the forgiving chaplain, Riddle was admitted to a transitional work-release program in 1999, after serving approximately a year of his sentence. He secured a position as a cook in Bryson City and also performed maintenance duties at an assisted living facility.

"I was determined not to fuck up," says Riddle, his voice resolute. "I vowed to work hard, keep my head down, and never steal again."

However, the fragile peace he had cultivated was shattered in July 2000 when a local produce vendor was brutally murdered during a robbery. The town was gripped by panic. Upon arriving at the seniors’ home, Riddle found his coworkers gathered ominously in the lounge. They glared at him as the team foreman, fueled by the town’s fear, launched into a barrage of accusations, citing Riddle’s alleged gang affiliations and extensive criminal record as evidence of his guilt.

"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 sheer ferocity of his declaration quelled the foreman’s bluster, but the incident ignited a deep-seated fear of wrongful persecution within Riddle. He immediately returned to his apartment, hastily packed his meager belongings into two backpacks, slipped into the surrounding woods, and navigated his way towards the Great Smoky Mountains National Park, with the ultimate destination of the Appalachian Trail firmly in his sights.

"Back then, I couldn’t have said what made me cut out on the trail like that," says Riddle. Given his history of evasion, his decision to embark on the AT seemed an improbable escape. Yet, he concedes, "I always felt better in the woods, so I guess maybe that’s what I was after."

Early in his journey, Riddle fell in with a group of straggling northbound (NOBO) hikers. It was during this initial period that he realized his own gear setup was conspicuously out of place. "I had this huge, external-framed backpack stuffed with crap like a 25 by 25-foot tarp, a cast-iron skillet, and a blue-speckled Walmart coffee pot," he describes. This behemoth pack, combined with a front-slung daypack, created an image of extreme over-encumbrance. "So I was insanely overloaded and looked absolutely ridiculous."

It didn’t take long, however, for Riddle to experience the profound generosity and supportive spirit of the AT community. Fellow hikers readily gifted him new gear and shared their meals. People opened their homes to him, offered him odd jobs for cash, and connected him with temporary work through friends and acquaintances. He formed a particularly meaningful friendship with the legendary, and now late, founder of Bluff Mountain Outfitters, Dan Gallagher, who assisted him in re-equipping himself in Hot Springs.

"People were just so good to me out there," says Riddle, his voice softening with gratitude. As he traversed mile after mile, "I realized that, for the first time in my life, it felt like I fit in somewhere."

As a self-identified "blue-blazer" (a term for those who hike extended sections of the trail) and a proud member of the "hiker trash" fraternity, Riddle would hike for a period, then hitchhike to a trail community when the urge to reconnect struck. He would find cash work and camp in the woods or stay in hostels or boarding houses where the need for credit cards and identification was non-existent. He carefully guarded his past, revealing little of his history and never staying in one place for too long. Riddle drifted north and south, guided by whim, an ever-present fear, and chance encounters. He forged connections with unconventional groups, such as the "Humble Hikers From Hell"—a hard-knock collective of military veterans, ex-convicts, and former bikers who sought solace and healing in the wilderness, often accompanied by revelry and the sharing of stories. At other times, he would hike in solitude, embracing the isolation as an opportunity for introspection.

"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, recalling moments of intense self-loathing. Conversely, he also experienced profound moments of transcendence: "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."

This cyclical pattern of evasion, self-discovery, and fleeting peace continued for three years. Riddle logged countless miles, virtually traversing every inch of the AT multiple times. However, as his time on the trail lengthened, he encountered an increasing number of hikers and began to gain a certain notoriety for his captivating stories and his unusually extended residency on the trail. This growing recognition made it increasingly difficult for him to maintain his anonymity.

"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. Bowen had befriended Riddle at an AA meeting in Bennington, Vermont, in the early 2000s and had invited him to spend the winter in an apartment located above 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 secure employment at a friend’s modest diner. The two men grew increasingly close, and one evening, the weight of Riddle’s past finally came to light. "When Larry told me what he’d done, it was such a shock I thought he was joking," says Bowen. It was only when he realized Riddle’s sincerity that he understood the depth of his friend’s burden. "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.’"

Taking Bowen’s profound advice to heart, Riddle set out hiking on the trail with the intention of returning to Bryson City around July 2003. At some point during this journey, he made a pivotal call to 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 probation officer informed Riddle that he owed $1,500 in restitution and that if he came down and paid it, he would be a free man. However, as Riddle drew closer to Bryson City, a pervasive sense of dread and suspicion began to consume him; he became convinced that it was a trap. Depression descended, and the memories of his past transgressions plagued him relentlessly. Suicide, he concluded, seemed to be the only viable answer.

"Then Hurricane Isabel brought me a miracle," says Riddle, his voice resonating with a newfound sense of wonder. "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 an additional 14 months in jail, a consequence of his inability to pay the restitution. Upon his release, he emerged with a clean legal slate and a clear conscience. He then set his sights on Damascus, Virginia, stating, "this place has called to me ever since the first time I passed through."

Riddle had no concrete plans for his future, but he knew one thing with certainty: "The AT had saved my life, and I knew I wanted to devote myself to that community."

He found lodging with friends and took on a variety of jobs, ranging from carpentry to cooking. His seamless integration into the community led to an offer for a low-rent rental home in the downtown area, situated about a half-mile from the AT, in 2006. Riddle launched a weekend flea market and began allowing trekkers to crash in a spare bedroom or pitch tents in his yard. Word of his hospitality spread, and Crazy Larry’s officially opened its doors in 2012. He later rebranded the establishment as Tow’s Place approximately a decade later, explaining, "people see the word ‘Crazy’ and think of a party spot, which created some problems for me now and then."

Overall, Riddle describes the hostel business as a profound 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 utilize the journey as a rite of passage from college to career; others hope to overcome the harrowing experiences of war or a painful divorce; still others celebrate retirement by pursuing a lifelong dream. And then there are those who hike as a means of grappling with past decisions—a struggle that no one understands better than Riddle himself.

"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 judgment can be really powerful."

Health challenges, including a heart attack in 2024, have necessitated a scaling back of Riddle’s operations. However, he remains steadfast in his belief that he will likely never fully close his doors to the transient community of the AT. "I owe the AT an immense debt," he declares. "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."