When The Hobos Roamed Small Town Iowa

 

"Scoopshovel" Scotty McDougall & Boxcar Betty, Hobo King & Queen

Iowa used to have a steady flow of uninvited guests, and nobody considered it a problem.

 

They arrived by freight train, usually without a ticket and with a pretty casual attitude about schedules. They stepped off somewhere near town, stretched, and drifted in like they belonged.

 

People called them hobos. It wasn’t an insult. Just a job description without the job.

 

You didn’t have to go looking for them. They were just… around. Sitting near the tracks. Walking the gravel roads. Cutting across a field. They had a way of moving that didn’t match the rest of town—slower, but not lazy. Like they weren’t in a hurry because they didn’t have anywhere to be.

 

You’d see one now and then, rounding the corner or on your front step.

The guy (never a woman—not sure they were allowed in the Hobo’s Union) looked like he’d been on the road for a little too long. Not dangerous. Just a bit worn down.

 

He’d ask if you had something to eat.

Hobo's riding the rails

That was it. Just a straight question, like asking for directions. And here’s the part that people today don’t get: we’d say yes without turning it into a situation.

 

Sandwich, maybe some chips, maybe coffee if there was a pot on. Wrap it up, brown bag it, done. He’d say thanks and head out, probably toward the tracks again, like that’s where his next decision would be made.

 

Nobody called anyone, or screamed about who showed up on their doorstep. It didn’t make the evening news because it wasn’t anything special. Just another day in the city.

 

That’s just how it worked. But not everyone saw it that way.

 

In 1905, the Ottumwa Semi-Weekly Courier took a dimmer view, calling a hobo “a man who is always going about the country, looking for work and praying that he won’t find it.” A few years later, in 1909, the Cedar Rapids Gazette warned readers that “hobo season” was on the way, describing some of the “old-timers and aristocratic hobos” as men who considered it a lasting disgrace to work—and refused to do so.

 

Other papers didn’t bother being that polite. One referred to them as “Wandering Willie’s,” like they were less a group of people and more a nuisance that drifted in with the weather.

A hobo asking for food

Still, for all the complaints, they kept showing up. And most of the time, people kept feeding them.

 

Fast forward fifty years, and the same knock turns into a group discussion, a quick scan of the security camera footage, and someone wondering if this qualifies as suspicious activity. You know it’s gonna be on Facebook. Maybe X or Instagram. Nobody’s wrong. It’s just a different world.

 

Back then, it didn’t feel like a risk. It felt like Tuesday. Which makes what happened in Britt, Iowa even better, because someone there turned the hobo lifestyle into an annual event.

 

In 1900, Teddy Wold had the idea that instead of shooing hobos out of town, they should invite them in for a few days. Feed them, let them rest, and treat them like they weren’t a problem.

 

So he did. And they showed up.

 

Clinton, Iowa, became a stopping point on the way to that first convention. A local reporter noted that when the men stepped off the trains, they didn’t rush into town looking for handouts. Their first stop was the Mississippi River.

 

Under a shade tree along the bank, they cooked their food, washed up, and—took the time to shave. When asked why that mattered, one hobo said: “We want to look the best we can.”

A hobo camp by the Mississippi River outside of Clinton

That first gathering became the National Hobo Convention, and for a few days every year, Britt turned into a destination for the men who rode the rails.

 

They set up camp in what they called the “hobo jungle,” usually near the tracks or on the fairgrounds. Fires blazing, coffee brewing, and conversations.

 

It didn’t really matter what they talked about. Because if you get a few dozen men together who’ve spent years riding the rails, you’re bound to hear some stories. And they were good at telling them.

 

They had their own system, too. Hobo signs—simple markings scratched onto posts or buildings. Not meant for everyone. Just enough to tell the next person what kind of welcome to expect.

 

Then came the part that really shouldn’t work but somehow did: the crowning of the Hobo King.

Hobo King John Mislen, the "Hardrock Kid"

You’d think it would be played for laughs. It wasn’t. They treated it like it mattered.

 

The king was usually someone who had been out there for years. Who knew the rail lines, the towns, and had a reputation. You didn’t win it by being charming. You won it by lasting.

 

The Great Depression had pushed thousands of men onto the rails. What had once been a lifestyle became a necessity. The convention grew, but the tone shifted—more need, more urgency, fewer illusions.

 

After World War II, things changed again.

 

Jobs came back. Highways took over. Cars replaced trains. Railroads cracked down. The entire system that had supported the hobo life faded.

 

Ben “Hobo” Benson first took the crown in 1938, beginning a run that would see him named king five times over the years.

Sharing stories at a hobo camp near the rail yard

In 1946, actor Errol Flynn even took a run at the title, claiming he was a hobo at heart. The judges didn’t buy it. He lost to Stenska “Skeets” Simmons, who, in his acceptance speech, apologized for his unpressed pants and the gravy stains on his vest.

 

In 1951, Eddie “Cannon Ball” Baker, 59, was crowned king—though some questioned his credentials after he’d spent nearly a year working as a cook in Des Moines. His queen, Sylvia “The Hitchhiker” Baker, didn’t seem too concerned about the debate.

 

By the mid-1950s, the convention still had its characters.

 

Scoopshovel Scotty McDougall took the crown in 1955, arriving with his companion Boxcar Betty. That same year, former queens like Hitchhiker Sylvia Davis and Boxcar Myrtle French were expected back.

 

But something had changed. Where the convention once drew 400 or more hobos, by 1955 that number had dropped to between 25 and 50. The Globe Gazette explained that the genuine hobo article had become scarce.

 

Even so, the crowds came.

Crowning the Hobo King at Britt, Iowa with a tin can crown and a blue velvet blanket

Through the 1950s, ’60s, and into the ’70s, spectators held steady at around 15,000 people. In 1970 alone, they went through 2,520 pounds of Mulligan stew.

 

Meanwhile, the number of actual hobos kept shrinking.

 

In 1962, King David, then 78 years old, said the old generation was disappearing. Men were getting married, settling down, “dropping out from bumming.” You just couldn’t find many new ones, and the old hobos were dying off.

 

In 1964, Sam “King” Cole took the crown—and had little good to say about Iowa. He called people there “snobbish,” complained they were stingy, and said he’d been treated worse there than in any other state.

 

1969, Slow Motion Shorty was king in 1969, with Myrtle French as queen.

 

In 1970, Hardrock Kid—real name John Mislen—was crowned king at age 68. His queen, Long Looker Mic Denseld, was 32 and not really a hobo at all. She was a sociology graduate student who described herself as a “hobo at heart” and was considering hopping a boxcar after graduation.

 

She returned in 1974 and was crowned again, this time alongside Steamtrain Maury Graham, who accepted his crown—a coffee can—and blue velvet robe of office.

The National Hobo Convention Parade at Britt, Iowa

Only six actual hobos showed up in 1973. The crowd watching them still hovered around 15,000.

 

By the time you get into the 1960s and ’70s, the classic hobo was becoming rare. We still saw them when I was growing up in the 60s, but they were fewer and farther between.

 

The convention leaned more toward memory than reality.

 

The title of Hobo King stayed, but it shifted. The last of the widely recognized “real” kings—men who had truly lived that life—were crowned in the late 20th century. After that, it became more about honoring the past.

 

The convention never went away. It still happens every year in Britt. There’s a parade, music, food stands, souvenirs, and a museum that tells the story—maybe a little cleaner than the real thing probably was.

 

It’s fun. A little odd. And it still draws a crowd. But it’s not the same.

 

That earlier version—where men moved across the country by rail, knocked on doors for food, and moved on to do it again the next day — has mostly disappeared. And that might be the strangest part of all.

 

Now we look back at it like it’s something out of another century. But it wasn’t. It was Iowa.

 

If you’ve ever said, “I remember that place”… this blog is for you.

 

I dig up the stories, the lost stores, the old Iowa you don’t see anymore. No clickbait. No junk. Just real nostalgia.

 

If you enjoy it, consider tossing a few bucks in the donation slot. It helps keep this thing going.

 

 Buy me a Big Gulp / Support Retro Iowa