Still Riding the Rails: Life as a Modern Hobo

By: Dave Roos  | 
Collinwood Kid serves mulligan stew with park district employees at a 2007 hobo gathering at Deep Lock Quarry near Akron, Ohio. While the glory days of freight trains have long passed in America, there remains a loyal contingent of hobos and wannabes. CHUCK BOWEN/AFP/Getty Images

Connecticut Shorty's father is buried in the National Hobo Cemetery in Britt, Iowa. When a hobo dies, they say he's “caught the Westbound.” Shorty's father, Connecticut Slim, rode the rails for 44 years before catching the Westbound in 1990 to the hobo jungle in the skies. Shorty didn't fully understand the lure of the hobo lifestyle until she began hopping trains herself in 1993.  

Shorty was in her mid-40s when she caught out on her first train from Dunsmuir, California to the legendary Roseville rail yard outside of Sacramento. A veteran hobo called Road Hog USA showed her the ropes — where to hide from the “bulls” (train yard cops), where the train stops or slows enough to hop on, what type of train cars to look for, and what to bring in your pack.


“I've never been afraid,” says Shorty. “It's always been such a grand adventure for me. My longest trip was from Staples, Minnesota to Whitefish, Montana over the Rocky Mountains and back.”

By the time she took the Rocky Mountain ride, Shorty was already in her late 50s. She and her traveling companion — a fella named Frog — hopped an intermodal container train. Those are the huge trains carrying double-stacked shipping containers, hardly the slow rolling boxcars of yesteryear. Shorty and Frog rode in the “well” or “porch” behind the shipping containers, exposed to the wind and dust and noise, but partially shaded from sun and rain.

“It's not comfortable!” Shorty laughs. “Nothing's comfortable. You're sleeping on metal floor, after all. But it gets you where you're going. You cross the country, you're out there with nature, you go through Indian reservations, over mountains — it's a wonderful adventure, and you're seeing America for free.”

For Shorty and her white-haired hobo friends, hopping trains is one of the last great traveling adventures. Shorty's not destitute or desperate. She has a home in Iowa and a winter refuge in Florida. For her, hoboing is a hobby and a way to honor her late father. But Shorty is only one type of modern American hobo.

Hobo culture is alive and well in the United States, but it's a far cry from the sanitized Halloween-costume version most of us are used to — the patched overalls, the charcoal beard and the red-bandana bindle (that's a bundle on a stick). Today's hobos are gutter punks and anarchists, crusty kids and societal dropouts trying to piece together an existence outside of civil society. And the best way to get there is to hop a train.


The Original Hobos

Very few people ride the rails full-time nowadays. In an ABC News story from 2000, the president of the National Hobo Association put the figure at 20-30, allowing that another 2,000 might ride part-time or for recreation.

That's a far cry from what it used to be. The very first American hobos were cast-offs from the American Civil War of the 1860s. When many soldiers returned home, jobs were scarce, so hordes of young men took to the newly built railroads to find their fortunes elsewhere. The name hobo is believed to be a shortened form of “hoe boy.” The original hobos traveled from town to town looking for odd jobs and menial farm work.


The combination of the Great Depression and the Dust Bowl in the 1930s forced millions of Americans to become migrant laborers. According to one estimate, the hobo ranks swelled to 4 million adults and 250,000 teenagers between 1929 and World War II. These steam-engine hobos crisscrossed the country looking for paying work and a hot meal, hitching illegal rides between, on top, underneath and occasionally inside train cars.

It was during this hobo heyday that the famous hobo code was created. Since many hobos were illiterate, they developed a system of signs — scrawled on fence posts and train crossings — to communicate vital information to fellow travelers. A picture of a bird indicated a free telephone. A cross signified a free meal if you professed religious belief. There's some question whether or not the hobo code was widespread (or even real), but it's proven to be an irresistible bit of hobo folklore.

hobo code
The hobo sign left at the entrance to this house (1934) means a hobo can get something to eat inside.
ullstein bild/ullstein bild via Getty Images

Shorty's father Connecticut Slim was one of these steam-era hobos and stuck with the lifestyle even after the transition to faster diesel engines in the 1950s. Hobo numbers dropped in the more prosperous post-war era, but rose again in the 1970s and 1980s with an influx of disillusioned Vietnam vets. Some of these vets formed the notorious Freight Train Riders of America, a drug-fueled rail gang accused of beating and even murdering hobos that encroached on their turf.

Today's hobos look very different than their Civil War forefathers or the Depression-era migrants, but they also share some striking similarities. When you've hit rock bottom, it seems, the best way out is on the back of a train.


Meet Dirty

That's not his real name, of course. All hobos have nicknames, but we chose this one to protect Dirty's true identity. Dirty started “traveling” when he was 19 and lived as a hardcore hobo for four years. You've probably seen people like him camped out in parks and panhandling outside bus stations. The look — overstuffed backpacks, filthy dreadlocks, ripped and patched clothes, skinny dogs, painful-looking piercings and tons of amateur tattoos. Yes, this is the face of the modern American hobo.

Maybe you've wondered, how did these kids get here? Are they homeless? Is this a lifestyle choice or is living on the streets their only option?


All of the above, Dirty says. Some kids like him grow up in a relatively stable middle-class environment and decide one day that's it's all a scam, so they head out in search of something different. Other kids are on and off the streets since childhood and have never known anything better. Even if the hobo lifestyle starts as a choice, though, it doesn't always stay that way.

“After a certain point, there's nothing to go back to,” Dirty explains. “Even if people did have a family that supported them, if you start tattooing your face and smoking crack they're going to start looking at you different. A lot of people have been pushed away from their families, but they've found a lot in common with their friends out on the streets. And that's their family now.”

Living on food stamps and handouts, sleeping in parks, getting wasted on cheap liquor and street drugs, and drifting from one city to the next, Dirty and his street family were drawn to the trains for the same reason all hobos are drawn to trains: they're free.

“There are different segments of the traveling culture,” Dirty says. “You can either be a ‘rubber tramper' — which means you have your own car — a classic hitchhiker or a train hopper. Only the train is completely free. Even when you're hitchhiking, it's still not free. You have to entertain the person that's driving with stories and stuff. Plus you have to stay awake in case they're a weirdo.” 

When you're traveling by train, Dirty says, you have total independence — assuming you get on the right train. Dirty and his hobo friends moved all over the country following a loose migration of crusty kids on the trail of music festivals and drugged-out blowouts. From Folklife Festival in Seattle to the Rainbow Gathering in Ocala, Florida to Halloween in New Orleans.

Full Width
Pat 'The Roaming Dreamer' Mulkern stands between freight cars with copies of 'Hobo News', in Hastings, New York, circa 1940. Mulkern was editor of the newspaper, which was aimed at homeless migrant workers.
Frederic Lewis/Archive Photos/Getty Images

The freedom and independence of the rails comes at a stiff price, though: serious physical danger. Dirty has friends who have lost limbs to trains. Others have lost their lives. Hopping on a moving train is hard enough, but even harder when you're drunk or high and hauling a huge backpack. The rule of thumb is to only hop a train if you can clearly make out each bolt on its spinning wheels. If it's too blurry — from speed or inebriation — catch the next one. Most modern train cars are sealed up anyway, so hobos nowadays tend to ride on the "porches" or spaces between containers, as Connecticut Shorty did.

Then there are dangers that have nothing to do with trains. Heroin overdoses, fights, muggings and even murder. Violence between hobos isn't the problem, but when you live on the streets beyond the protective bubble of society, you're exposed to all types of people, the good and the ugly.

Still, Dirty talks with pride about the “hobo code,” the set of community standards that guides life on the rails and offers a form of group protection. Never break into a boxcar, for example. It shows disrespect for the people who work the trains and it prompts tighter security. Hobos will tell you there's a difference between being a hobo and being a tramp: A hobo works and wanders, while a tramp only wanders.

Hobos look out for one another, especially for the women, and lay down street justice on offenders.

“If there was any kind of sexual assault, you'd be lucky to get out alive,” Dirty says. “We take that kind of thing very seriously.”

Dirty retired from the hobo game when he sobered up for a girlfriend, but he still stays in close contact with his extended hobo community. Hobos love Facebook, it turns out. And they have their own underground social networks like the (warning: not remotely safe for work) Tumblr Look at this f***ing Oogle. In between the obscene photos and drunken displays are some heartfelt pleas from fellow travelers. Have you seen this guy? We're worried about him. Call this number if you know where he is.

As much as he recognizes the depravity and danger of the hobo lifestyle, Dirty values the friendships he forged in the streets and on the trains. He describes his four years as a hobo like a tour of duty in the military.

“We're all ‘vets' out there,” Dirty says. “And my best friends are people who have been through the same experience. Those are bonds we can never break.”


Hobo Heaven

Every August, hundreds of hobos and hobo aficionados from across America gather in Britt, Iowa for the National Hobo Convention. The convention has been held in this tiny whistle-stop since 1900, when the town fathers welcomed three Chicago hobos looking for a new home for their annual get-together. In addition to the annual convention, the town celebrates Britt Hobo Days, a long weekend of parades, concerts, fair rides and fried food attended by more than 20,000 visitors. 

Connecticut Shorty hasn't missed a National Hobo Convention in 25 years. She proudly mentions that she was elected National Hobo Queen in 1992 (her sister, New York Maggie, won the honor in 1994). Hobos start arriving in Britt a week a few days before the convention begins. They come in motor homes and on motorcycles, and some still ride the train, hopping off at nearby Mason City and hitchhiking to Britt. They set up a “hobo jungle,” a hobo encampment in a city park, and light a ceremonial fire that burns steadily through the whole weekend.


There aren't many real hobos at the National Hobo Convention. This is more about preserving history than passing the baton to the next generation. Shorty gives tours of the National Hobo Cemetery and shares the stories of steam-era hobos like her father, men who took to the rails out of necessity and found an odd sense of home and community in that rambling world.

The hobo lifestyle is a curious thing to celebrate, but it speaks to something quintessentially American — a spirit of rebellious independence, hardscrabble survival and the hope of something better a little further down the line. As grim and desperate as the lifestyle can be, as long as there are trains, there will probably be hobos.