Before diving into this piece, I want to share that it’s an abridged version of my full article in American Heartland Magazine. You can read the entire story, along with more of my work, at https://americanheartlandmagazine.com. I hope this glimpse inspires you to explore more of the heartland’s hidden stories and unexpected places.

Back in my freshman year of college, I found out about the National Hobo Convention in Britt, Iowa, and was immediately intrigued by it. I mean, what could a hobo convention even be? I didn’t even know hobos were still around. After it rattled around in my head a while, I made a quiet vow to myself that someday I’d drive up and see it with my own eyes. This year, I’m going to follow through on that old promise. 

Driving North on I-35, I notice that a railroad has sneakily appeared, running alongside the highway. Its well-worn tracks hint at a long history, and I wonder if it is the same line that once carried hobos to Britt. Maybe it still does. It’s easy to imagine them perched in groups on the edge of weather-beaten box cars, the wind whipping their faces, their eyes scanning the horizon. I feel some kind of connection—like my path is crossing with the hobos for the very first time here. After a few more miles, the horizon breaks, and a bright red water tower rises into view. Its tall frame makes for a nice change of pace after hours of staring at the flat Iowa landscape. One word is painted across it—the name I’ve been chasing: Britt. But as I draw closer, I notice something else. Something written just beside the name: Hobo signs. They are a marker, of sorts, that tell me I have reached the gathering grounds of those who took off with a restless heart, and a need to roam just as I have. 

Hobo signs are, supposedly, a kind of road-worn sign language developed by those drifting along the rails to share important information with each other. A circle split by two arrows, both pointing to the right, is a clear message: “Get out fast.” A crudely drawn cat signals that “a kind-hearted woman lives here.” Other symbols might indicate if a campsite is worth stopping at, if the law is thick in the area, or if a nearby homeowner might have a little something to spare. For almost every situation, there is a hobo sign to go along with it. It is a language hidden in plain sight—ignored by the ignorant but recognized by those in the know. 

But here’s the thing—notice I said “supposedly.” There’s a good reason for that. Although reports of hobo signs date back as far as hobos themselves, whether they were ever widely used is still up for debate. Some argue that they were the creations of imaginative writers looking to add a little romance to the harsh life of a hobo. Some hobos even admitted that these signs were more legend than fact back then, that they were just the clever inventions of outsiders rather than something you’d actually see written under a bridge or on a barn wall. There’s no real way to know the origins, but they seem to have stuck anyway. These glyphs have been folded into the ever-growing lore of hobos. 

I pull over to the side of the road to look up what the symbols on the water tower mean. They say that “this is the spot” with a “fresh-water campsite” and a “train stop.” 

My truck rolls across the train tracks as the iron creaks beneath me. Ahead, the town’s welcome sign waves me on. I’m not a hundred feet past the wooden sign when I finally catch sight of them—hobos, the real deal. There are a few of them lounging in the shade, like time is nothing but a vague notion. But then the scene opens up—a collection of colorful tents, rusted vans, and dusty RVs are huddled beside the railroad tracks that led me into town. It dawns on me that I have found the hobo jungle: that haven where the drifters and dreamers collect to feel a brief sense of community. I ease off the gas as I let my truck slow to a crawl. Right in the heart of the camp, there is a firepit. Its blackened logs tell me that it had been used just last night. I can picture them there; hobos gathering as the sun goes down, swapping stories, and singing songs as the slow crackle of the fire serves as their soundtrack. I wonder what those stories sound like. Are they harrowing stories of hopping onto freight trains, or perhaps just quiet reflections on lives that have slipped through their fingers? 

The jungle is different than I envisioned. I’m not exactly sure what I expected, but the tents that look fresh out of a sporting goods store are a surprise. Then, there are the vans and RVs. They seem out of place here. Still, these modern additions to the hobo ways have not softened the edges of this place. 

Parking my truck on a shady street, I eagerly walk towards the sound of the parade in the distance. Candy flies from the backs of golf carts, fire trucks switch on their lights, and kids scramble in the early morning sun. Then a flatbed truck comes rolling around the corner, carrying a ragtag group of musicians who look like they’ve lived a life or two. The singer, perched up high, belts out a song with a voice full of grit and soul. His lyrics are simple and steady—he is a hobo, not a bum. 

You’d be forgiven for not knowing the difference between a hobo, a bum, and a tramp. Most people lump them all together, never giving a second thought to it. But if you ask a hobo, the difference is no small matter. The writer H.L. Mencken famously put it best in The American Language: “A hobo or bo is simply a migratory laborer; he may take some longish holidays, but soon or late he returns to work. A tramp never works if it can be avoided; he simply travels. Lower than either is the bum, who neither works nor travels, save when impelled to motion by the police.” 

That all boils down to something pretty simple—hobos are willing to put in the work, while tramps and bums are not. To some, that might sound like splitting hairs. After all, they all live on the fringes, without a fixed home, scraping by in ways you can only imagine. But, to a hobo, the difference is everything. The term is like a badge of honor. It’s something that separates them from the idle drifters and the down-and-outers. For them, it’s about earning your place, even if that place is on the move. 

The first hobos were often Civil War vets—guys who didn’t want to return home for one reason or another after the war ended.  Instead, they hitched rides on slow-moving freight trains heading West on the newly laid tracks, chasing new frontiers and opportunities. I suspect that many weren’t just looking for work but also fleeing from the ghosts of battle and the horrors of war. They unknowingly paved the way for generations of migratory laborers to get where they needed to go. From then on, anytime things got tough, hobo numbers surged. When the economy took a dive, the rails were flooded with men. The cycle of recessions in the late 19th century meant that by 1906, according to Professor Layal Shafee, there were around 500,000 hobos across America. Six years later, that number jumped to 700,000. By the time of the Great Depression and the Dust Bowl, some have estimated that as many as 4 million people had become hobos. Jobs were nowhere to be found, money was even scarcer, and hope was drying up like the land itself. So young men did what they had to—they snuck onto freighters. They disappeared behind the horizon, searching for a more prosperous corner of the country. 

As the parade rounds the corner and the last notes of the band fade into the distance, I feel the true pulse of the festival kicking in. Families fold up their lawn chairs and gather their kids and candy into chaotic bundles with a well-rehearsed ease. The crowd, no longer held in place by the pageantry, begins to spill down the street like a lazy stream finding its course. I fall in with the slow current of people making their way towards the main drag. 

First on my list of stops is the Hobo Museum. Walking North on Main Avenue, I find it with no problems. It’s hard to miss. From the outside, it appears to be an old movie theater converted into a home for hobo memorabilia and artifacts. I want to get in there before the crowd swells and soak up some of the history before it gets diluted by the noise.

I spend a while poking around and by the time I step out of the museum, I feel like I’ve brushed against the edge of an unfamiliar world—the hobo’s world. Inside, I had avoided the dimly lit nook in the back where an informational film flickered on a screen. I know all too well the dryness of such presentations. Instead, I lingered among the relics, weathered tools and keepsakes from transient lives. They spoke to me more than any documentary could, offering a glimpse into a life lived on the edge of society. Seeing it all laid out in front of me made me feel like I was standing on a mountain, gazing down at a landscape stretching out endlessly, vast and unknown. But I know this view is only the beginning; to understand, I have to venture down into the valleys.  It’s time to leave the overlook and meet the world on the ground. I know that I need to find the hobos themselves—see them up close, hear their voices, and perhaps even catch a story or two. 

I’m in the thick of it now—right where the coronation is set to begin. There are hobo conventions scattered all around this country, but Britt is the crown jewel of them all. This is for a couple good reasons. The coronation of the Hobo King and Queen is certainly one of them. From what I’ve gathered, this is the only place where such a ceremony happens. It’s a playful tradition, sure, but there’s something deeper to it—an acknowledgment that goes beyond simple appreciation. This convention has taken place since 1900, and a new king and queen are crowned each year. For a moment, this community of misfits gets its own touch of royalty. It’s part of what makes the whole thing feel special, like you’re watching history and tradition blend into something that’s both whimsical and oddly reverent at the same time. 

Right now, it feels more like a block party than a regal affair. Townsfolk and hobos alike have all gathered in this small park to tell stories and laugh over steaming bowls of mulligan stew. The stew, ladled generously from towering black pots, is a hobo staple. Traditionally, it is made from whatever ingredients happen to be on hand. Today, it resembles a hearty vegetable soup. Its smell, though, is harder to define. A mixture of root vegetables, odd cuts of meat, and the well-used pots in which the soup simmers gives the air a distinct earthy fragrance. The smell seems to seep into the park itself, blending with the grass and the summer breeze.

Everywhere I look, I spot hobos. There are more of them in this park than I have seen all day long. Even still, I’m having trouble figuring out who to approach. Then out of the crowd, an older woman comes bouncing past me. It takes a moment for me to realize that she is actually dancing quite literally to the sound of her own music. And sure enough, there’s no mistaking it—she looks like a hobo. 

I go for it. “Nice moves,” I call out.

“Well, thank you, young man!” she replies, still dancing along. 

“You wouldn’t happen to be a hobo?” I ask, half-joking. 

She spins to face me fully with a wide grin across her face. “Why yes I am! Name’s Ramblin’ Rose. I’m the crumb boss!” 

“Crumb boss?” I ask, a little caught off guard. 

“The camp cook! Head chef!” She exclaims proudly with a laugh in her voice. 

I explain that I’m here to talk to some hobos, and without missing a beat, she starts pointing people out. 

Thanks to Ramblin’ Rose, I have a few people in mind to talk to. Now, it’s just a matter of picking one. Scanning the crowd, my eyes land on a pair standing off to the side—a man and a woman. The man is tall and a bit lanky, with a large, unkempt beard on his face. His overalls are patched with bits of spare fabric. Beside him, the woman is dressed head-to-toe in black, and her face is framed in dark make-up that contrasts the whimsical colors and atmosphere around us. Ramblin’ Rose had mentioned that this is their first year, and they are helping her with the cooking. They seem approachable, and given that we’re all newcomers here, it feels like a perfect chance to talk. 

I walk towards them and they greet me with those slow, deliberate smiles you only get from people who have seen enough to know what truly matters. I introduce myself and explain what I’m doing here, and the man nods, “Well, I’m Irish Devil.” He motions to the woman next to him, “And this here’s Star Dragon.” 

Before long, we are deep in conversation. I ask them if they see themselves coming back to Britt next year. They glance at each other, and it feels like I’ve struck something more significant. “I’ll probably be coming back ’til the day I die,” Irish Devil said softly with a certainty in his voice. “This place… here, you’re welcome. Out there, people don’t always want you around. But here, you get fed. You’re safe. You belong.” Star Dragon nodded slowly, her eyes softening. 

People are beginning to gather now, ready for the coronation, so I know I don’t have much more time to talk. “Is it dangerous? Being a hobo, I mean,” I ask. 

Their smiles fade a bit, their faces darken, and the mood shifts. Star Dragon speaks first, her voice firm. “There’s bad people out there. Some pretend to help you and wait until you fall asleep and… Well, you can guess.” 

Irish Devil takes over with a story that stops me cold. He talks about a man who offered him food and shelter one night, a seemingly kind gesture. But the man’s intentions were far from good—he wanted to kill him and maybe eat him. Irish Devil’s eyes gleam as he recounts the close call. “Knew the guy was a tattoo artist, so I asked him for one. He got so wrapped up in inking me, he forgot all about his plans,” he says. Irish Devil raises his wrist, revealing a faded mark. “That’s the tattoo,” he says, pointing to it. 

Life as a hobo isn’t just about dodging the worst kinds of people—the thieves and killers. Danger comes from everywhere. Riding the rails means squaring off against the raw elements. You fight the bitter cold that cuts straight through your skin and the heat that seems to bake you from the inside out. Hobos have to learn real quick that survival depends on keeping your wits and knowing just how far you’re willing to push yourself. 

Almost poetically, the very thing that allows hobos to get around can also be their own untimely demise. Irish Devil and Star Dragon tell me about their experiences hopping onto trains, and I get the sense that there is nothing romantic about it. It is survival wrapped up in a roll of the dice. Gone are the slow-moving freighters marching their way across the landscape. Now, diesel engines have taken over where steam once ruled, making the whole business of hopping trains a lot trickier—and a hell of a lot more dangerous. Yet, Hobos still hitch rides on trains that roar across the landscape like beasts, their speed unforgiving and their steel bodies merciless. One wrong move and that jump could be the last thing you ever do. The stories about guys slipping and falling under the blade-like wheels of trains aren’t just legends. They are brutal truths of hobo life. 

Behind me, the coronation is gearing up to start. Mics are being checked, and people are finding their seats, but I’ve still got time for one last moment with these hobos who’ve let me into their world. Their stories swirl through my head like smoke from a fire. Clearly, hobo life isn’t easy. It’s brutal, relentless, and unforgiving. But beneath that hard exterior, there’s something so much more. Their history, the codes they live by, and the essence of what it means to be one of the few hobos still remaining give meaning to the struggle. To a certain extent, I get it. Yes, it’s a strange kind of brotherhood, but you start to see how such a rough life could be worth it. Hobos are tied to something bigger than themselves, whether they know it or not. They are pieces of a living relic, still acting like this country is the wild, untamed place it used to be. It’s sort of… admirable. 

I search for one last question to ask them, but nothing comes. Instead, I just say what’s on my mind. “Seems like a hard life.” I tell them plainly. 

They both nod with no hesitation. I don’t see any regret in their faces—no second guessing. Just a quiet acceptance. There is a deep, unwavering understanding of the path they have chosen. Irish Devil looks at me straight in the eye and speaks. His voice is calm, but a fire burns just under the surface. “I don’t want it easy,” he says. And that’s it. That one line says more than any deep philosophical musings ever could. It sends chills through me, not necessarily because of his words but because of the fortitude behind them. 

The coronation starts with a solemn prayer for the hobos who’ve caught the westbound, a poetic description for those who have died since last year’s gathering. I find a spot to hunker down, close enough to feel the weight of it all and settle in to watch. 

https://americanheartlandmagazine.com