The hobo inspiring a new generation of restless spirits (1 Viewer)

Matt Derrick

Semi-retired traveler
Staff member
Aug 4, 2006
Austin, TX

After leaving his small town as a teen, 'Huck' hit the road to hitchhike, hop trains and live by his own rules. Now he’s helping other vagabonds navigate a society they see no future in.

You don’t choose your name as a hobo. You earn it. Steven Boutwell gained his while working with another travelling kid on farms in Washington State. Something about his adventurous spirit and southern drawl inspired the boy to start calling him Huckleberry, after the Mark Twain character.

“He pegged me pretty easy with the name,” Huck says now. “I eventually said, ‘You have to drop the ‘berry’ part, so call me Huck or something.’ Then you go to another town and the name just comes with you.”

Huck is a hobo, one of America’s modern-day vagabonds who travel the States by hitchhiking and hopping trains with no set job or home. Like his namesake, Huck had a difficult time fitting into society as a teenager.

Growing up in a small Christian town in Alabama, with a population of just over 1,000, he felt like an outsider in his community. “Me and that town couldn’t get along.”

Huck also smoked weed as a teen, which led to a stint in jail that tarnished the reputation of his mother – a local public school teacher. Given the lack of educational or employment opportunities, the 19-year-old packed his bags and headed to California without looking back.


“Where do you go when you just want to escape?” asks the 36-year-old now. “San Francisco. That’s where the gold-miners of the 1800s went; that’s where the hobos of the Depression era went; that’s where the hippies of the ’60s went. That’s where I went.”

Since then, Huck has travelled tens of thousands of miles on freight trains and in the back of strangers’ cars. Hundreds of nights have been spent on the street. He’s begged for food. He’s been spat at and verbally abused by passersby.

There have been countless days of hard labour on farms. But he’s also seen a side of America that most never will, all while living what he sees as a fulfilling life on the fringes of society.

Almost unwittingly, Huck became part of a subculture that began in the late 1800s, back when ex-servicemen searched for work following the Civil War. The word hobo is said to have come from ‘hoe boy’, referring to the tool these seasonal workers would carry.


But after travelling over 2,000 miles, Huck arrived in California with no connections and no idea of what he was going to do – just driven by the idea that he needed to escape something.

“It was a real struggle for the first few months,” he says. “I was living on the streets and in city parks, having to dodge or deal with crazy bums, thieving drug addicts, harassment from the cops. But eventually I started meeting other travellers that had much more experience than me. They taught me how to find jobs, hitchhike, hop trains.

“As someone that always liked working but also wanted to travel, it just happened naturally that I became a hobo… Some people ain’t meant to stay in one damn place, one damn job, one damn small circle of friends, one damn repetitive daily cycle. We want change. We want to experience.”

His first migratory job led him to the fish canneries in Alaska, followed by a spell in Washington for the apple season. Once he’d raise enough money, Huck would hop a train or hitchhike down south and hibernate for the winter. Then, come late spring, it’d be time to get back up to Alaska and start over.

Though cultural figures like Jack Kerouac have romanticised the idea of a freewheeling figure living an alternative American Dream, Huck admits there’s a much darker side. “If we’re not the black sheep of the family, the family itself is the black sheep,” he says.

“A lot of the kids out here come from broken homes – parents who were alcoholic, parents who were abusive – or were abandoned. We’re kids who just fell through the cracks of society and wanted to find a way to exist outside the norms that pushed us out.”


As many as 1.7 million young people experience homelessness for at least one night a year in America. Huck was still a kid when he became part of that statistic but he’s noticed that hobos are only getting younger.

“I made the decision to pack my bag and leave Alabama but, at the same time, when one is left with no choices, is that really a choice?” he says. “There’s so many young people dropping out of society and just hitting the road. They have no faith in what the future of this country holds for them.”

To help others pursuing the hobo life, Huck created the r/vagabond community on Reddit, the internet forum, where over 100,000 members can share stories, tips and pictures of their adventures.

Huck is now in his second decade of navigating those experiences. For a while, he’d drive from town to town with other travellers doing homeless outreach as Volunteers on Wheels.

These days he’s working on a remote marijuana farm in California, living in a little cabin with just his dog, a small air mattress, a chair and a little writing table. “That’s the substance of my life,” he says. “I’m still hoboing, just trying to do it in a better way.”
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I'm a d-bag and got banned.
May 12, 2018
Minneapolis; Going West
I grew up in a similar situation, except I have lived in a slightly more populated (and most likely dangerous) town. Toledo, to be exact. I've been in and out of homelessness for 4 years now. Grew up in a broken home, with an abusive father, and a neglectful drunk of a mother. I've lived off scraps and borrowed money I (eventually) payed back, but I've felt awful asking in the first place, but being in need or homeless isn't a choice, and I needed money to get the things I needed to survive, Which I personally think is a flawed state of being. I wanna experience what the world has to offer and travel from town to town, meeting awesome people, sharing stories, and learning new things.

This gives me a bit of inspiration to actually go through with it, and maybe I'm not so crazy for needing an "escape" from all the stress that I'm bringing upon myself by staying in the same place, or at least trying to. I've been so concerned with keeping a roof over my head because that's what people look for when they think of a home, or when they need a sense of security.

But I want to break the cycle, and the shackles of my depression and find the person deep inside me I've been looking for beneath the rubble of my self doubt and loathing. That's why I wanna leave Ohio, and not look back... at least for a few months.

Thanks for the article, Matt. I'm new to StP but I feel a sense of wonder seeing all these stories and it fills me with the warm & fuzzies on some of my darkest days, when I have doubts I'll ever leave.

Eng JR Lupo RV323

Jerk bouncer with an attitude
Staff member
Dec 26, 2010
559, Fuckno California
I happened upon the bus sometime in October of last year sitting broken down in Redway California, northwest of Garberville. Pretty sure that's as far as it made it, which seems pretty damn far all things considered.

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