The Hobos of Instagram
Steele's travel companion, Kevin, with phone. Photo courtesy Molly Steele


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The Hobos of Instagram

They're trading their flip phones for iPhones, browsing r/vagabond, and bringing an age-old tradition of trainhopping into the Information Age.
April 22, 2015, 2:30pm

They're trading their flip phones for iPhones, starting Instagram accounts, browsing r/vagabond, and bringing an age-old tradition of trainhopping and tramping into the Information Age.

Take traveling photographer Molly Steele, who was recently part of a group of hobos taken into custody onboard a freight train near El Dorado, Kansas.

"We almost got caught one day, and then decided to get back on the train like a day and a half later," said Steele, 26. "We were on the train for like 30 minutes before we were pulled off."


Thanks in part to the support of a sympathetic local politician the group met while renting a car, the authorities agreed to defer prosecution and drop the charges if Steele and the others stay out of trouble for three months, Steele said.

"We went from being criminals to being like the grandchildren of the town," said Steele, who shared her mug shot with her more than 30,000 Instagram followers.

On the train, where she was only able to bring a limited amount of equipment, her iPhone was an essential companion. GPS-enabled maps let the group know when it was safe to pop their heads out of the train and their phones generally helped pass the time they spent inside, hiding from railroad workers.

Eight decades after the Great Depression, there are still those Americans who get by doing odd jobs or busking for spare change, traveling the country in beat up cars and sneaking their way onto freight trains. But just as they've long since traded their bindles for modern backpacks, vagrants, like the rest of the world, have eagerly adopted the internet, smartphones, and other affordable, portable digital tools to help them find short-term work, navigate with GPS and simply stay in touch with family and friends.

Call it Hobo 2.0.

"We're kind of drawn to the life of electricity because it is so helpful to our lifestyle that we can't avoid it"

"When I first started, a little over 11 years ago, we were doing pretty much the same thing hobos have been doing for the past 125 years," said one frequent trainhopper and hitchhiker who goes by the name Huck. "Our maps were on paper. We communicated with each other word [of] mouth. We would leave codes and monikers up on buildings."

Arriving in a new city meant going from door to door, looking for the kind of manual labor jobs now mostly found on Craigslist. Google Maps hadn't yet launched, and few in the lifestyle could afford cellphones of any kind.


"We didn't give a shit about electricity, because we didn't have anything that even took electricity," Huck said. "Now, we're kind of drawn to the life of electricity because it is so helpful to our lifestyle that we can't avoid it."

For reasons including fear of prosecution—"My lifestyle is freakin' illegal," he told me, referring to his unauthorized freight train rides—Huck, who told me he's 33, doesn't like to disclose his real name.

But he's still become something of a minor internet celebrity after founding r/vagabond, Reddit's 10,000-member forum for "hitchhikers, trainhoppers, backpackers, rubbertramps [who travel by car or van], squatters, tramps, and other houseless travelers."

He and other members have posted questions and answers on topics from getting lucrative seasonal work at Alaskan seafood canneries to picking a cell phone with a long battery life.

"That's key for a hobo or a vagabond is battery life on a device, because we can't always charge our devices," said Huck. He travels with a long-lasting and lightweight Kindle to store maps and survival manuals and a solar-powered USB charger and portable battery pack to recharge his phone.

Like most travelers who spend a lot of time on their feet, he knows exactly how much each piece of gear weighs and how much room it takes up in his backpack. He also knows off the top of his head how long it takes to get a charge out of each device and how much power the battery pack can hold.


Social-sharing communities like Reddit let Huck and countless other hobos get up to date on the news quickly without using too much precious battery life, he said.

Huck's own /r/vagabond forum received a boost in popularity after he was featured on the Reddit podcast Upvoted and in other media, but it's just one of several sites providing an online home to wanderers with no fixed place of abode.

Wiki sites HitchWiki and TrashWiki provide community edited guides to sites around the world for hitchhiking and dumpster diving. Another forum site called Squat the Planet calls itself "the world's largest social network for misfit travelers" and got its start around 2001, according to founder Matt Derrick.

"It kind of initially started out as a train hopping website almost exclusively because that's what I was doing at the time," Derrick told me. Derrick started the site as more of a blog, and it gradually expanded into a message board for underground travelers, he said.

Now, Squat the Planet offers forums for travelers to find rides, goods for sale and trade—one not terribly atypical thread offers to swap a paintball gun for a fiddle—and places to stay, along with advice on squatting and hitchhiking and other resources.

"To me the most valuable thing I have taken from the forum isn't any specific piece of advice, it's more the sense that everything is possible," wrote Sally Randle, a United Kingdom-based moderator on the site, in an email.


Randle, who primarily lives and travels in a van, said the site helped her learn about experiences different from her own, like trainhopping, which isn't widespread in the UK.

"As a [lone] female traveller hearing others' experiences and sharing my own made me feel confident that I'm not the only one doing this and actually I probably won't be murdered in my sleep," she said.

Derrick, the site's founder, first got started in the lifestyle a bit "by accident," he said, when his car broke down in Oregon in the midst of what he thought would be a road trip to Los Angeles.

"I ran into some other, like, punk rock kids, and they were hitchhiking and riding trains and stuff, and I was like, take me with you," he said.

That was in the late 1990s, and he soon found himself spending the better part of a decade hitchhiking and trainhopping, often fixing computers and doing web design and other IT work to support himself. It was a skill he picked up growing up without much money, cobbling together gaming PCs out of thrift store castoffs, he said.

In the last few years, Derrick has upgraded to bus travel and the occasional flight, though he'll still hop a couple of trains a year, he said. And in the time he's been on the road, he's seen the internet and sites like Squat the Planet grow in popularity among travelers: the majority of forum accounts were created in the last five years, he said, and mobile traffic's exploded since 2012, as travelers have picked up smartphones and tablets.


"Unfortunately, we do have a younger generation that's never not known the internet, so that does kind of lead to what we call on the website 'spoon-feeding,'" he said. "People come on the website and occasionally demand to be spooned information, because they think that's what the Internet is. They don't understand that it's like a community you participate in, and you can learn incredible information from, but you've got to participate."

But many users seem to be far from deadbeats: the ride-sharing board typically features nearly as many offers of rides as requests. A sex-and-romance forum offers sympathetic ears for travelers who might otherwise have few around, along with one long-running thread that reads like the hobo version of Penthouse Forum. And members often join the website after they've already been traveling, eager to share what they've learned with a likeminded community.

"I grew up with the internet, and sharing has always been a part of my life because of the age that I am"

One 28-year-old who posts under the handle Viking_Adventurer said he took to the road in late 2013 after going through a divorce.

"I've always loved traveling, and I kind of hit a crossroads in my life," he told me. "I had just gotten divorced, and I was living in a small town that I moved to when I got married, and just she and her family already lived there."

He's hitchhiked from Southern California to New Orleans for Mardi Gras, where he squatted in a dilapidated house apparently abandoned to the elements after Hurricane Katrina. Along the way, he made stops in Arizona and Texas, and spent a few months living in Seattle, where his brother helped him find work at a travelers' hostel.


At one point, a friend he was visiting told him about Squat the Planet.

Since then, the forum's helped Viking_Adventurer find concrete information about cities he's visited, "what streets to look out for in this city, what restaurants are friendly to people that haven't showered in a week and are carrying a giant backpack," he said. At the time we spoke, he was in the process of coordinating a ride up the West Coast from Thousand Oaks, California, looking to visit Seattle for his brother's birthday.

"The reason I'm in Thousand Oaks is 'cause I was emailing someone about a rideshare to Bend, Oregon, and I'm still waiting for his reply," he said. "He was leaving Thousand Oaks, heading north, so hopefully I can get a ride with him."

Another Squat the Planet member named Kevin O'Sullivan, who posts under the name Highwayman, said he's used Craigslist and Squat the Planet's own rideshare section to find transportation, and CouchSurfing to find places to stay.

"Usually from the rideshare and before I arrive at whatever pre-determined destination that I am getting a ride, I will use Google Maps to check for railroad yards [to hop trains], check that area's Craigslist in hopes of piggybacking rideshares and also check the Megabus app to see if that location has any cheap buses to keep heading in that direction," he wrote in a private message on the site. "These things are constantly being done over and over again regardless of what mode of travel I am currently on."


He's used online maps to find campgrounds and public restrooms, truck rental depots where unlocked vehicles can serve as shelter from the elements, places with showers and, naturally, outlets to charge his phone. And if his phone stops working or he can't get a signal, he'll fall back on a paper AAA map or visit a public library.

O'Sullivan said he's not homeless or a full-time traveler—he has an apartment, and a family he stays in touch with from the road. A self-described Catholic anarchist—"If I didn't have a wife and children, most likely I would be a Catholic monk or friar and have zero earthly possessions," he wrote—he takes to the road to visit holy sites and attend punk rock shows, sometimes volunteering at nonprofits along the way.

But while many travelers are, at least to some extent, itinerant by choice, forum operators still look to strike a balance between providing information to let new travelers stay safe and making the lifestyle too appealing for teenagers without the skills to stay safe.

"When we first started, it was throw out your fucking thumb or jump on the boxcar, and that was all the information you had," Huck said. "I didn't get to go to YouTube and watch trainhopping documentaries and get this visual glimpse of what the lifestyle would be."

That led to minor mishaps like newbies hitchhiking on deserted roads or jumping on a train headed in the wrong direction. It also led to some serious injuries over the years from fast-moving trains.


"There were kids that had gotten killed because they didn't know what they were doing," he said.

Huck said he's glad /r/vagabond can publicize the dangers as well as the glamorous side of his lifestyle. The forum still bans publication of crew change tables, or guides to when and where freight trains stop to let railroad employees on and off. The guides have traditionally been carefully compiled by trainhoppers and passed along only to trusted associates, partially out of fear that making it too easy to ride the rails could get amateur hobos seriously hurt, he said.

Since riding the rails is also illegal, trainhoppers also worry a rise in the number of less-than-stealthy attempts could lead to a crackdown by railroad officials, making trips riskier for everyone.

Still, forums, blogs and social media also provide a way for travelers to share their experiences with friends and family, and the interested public at large. Huck's done multiple Reddit Ask Me Anything question-and-answer sessions, and, like many travelers, shares pictures of his experiences on Instagram.

Vine courtesy Molly Steele

For Steele, sharing pictures from her trips online just seemed natural, even once she was arrested.

"I grew up with the internet, and sharing has always been a part of my life because of the age that I am," she said. "It's the age that I live in. It just feels normal to share photos of what I'm doing."

Steele said she transitioned from living off savings and posting pictures on Instagram purely for fun to supporting herself by selling prints from her website and doing the occasional commissioned shoot.

"I don't think I would be a photographer or doing what I do if it wasn't for Instagram," she said.

She usually travels by car, bringing camping equipment and picking destinations more or less spontaneously.

"I had been working so much and was planning to buy a [new] car," Steele said, "but instead of buying a car I just quit my life and started doing whatever the fuck I wanted."