Hobo tips on riding rails
Jason Hoffman/Thrillist
Travel

America's Greatest Living Hobos Share Their Tales of Riding the Rails

Cheapskate travelers will find no shortage of tips on how to travel on a budget: the best time of year to book flights, how to rent out your home, arcane websites that promise half-off on flights that only board for three hours on the morning of the winter solstice, and so forth. But the ultimate cheap travel move? Don't pay. For anything.

Sounds simple enough, but of course nothing in this life (hack) comes for free. For guidance we turn to the ultimate freeloading traveler -- the train-hitching American hobo.

The tightest advice we got? "I tell people the best way to enjoy traveling is always the safe way," says Connecticut Shorty, a former hobo "queen," as crowned at the National Hobo Convention that takes place the second week of August, every year since 1900, in Britt, Iowa. "Hopping freights is illegal and dangerous."

But those enormous drawbacks don't deter everyone. Let's say you did want to ride the rails, and to see America as workers and travelers and drifters have since the 1800s? Well, you'd definitely want to listen to these hobos, each respected enough to have been elected king or queen by their peers, each telling their tales here in their own words. Don't try this at home, maybe. Or, hell, maybe do -- speeding away with a cold wind in your face, a metal-on-metal clackity-clack offering the soundtrack to a journey that people do still, to this day, run out to the rail yard to make happen.

Hobo tips for riding the rails
Jason Hoffman/Thrillist

Ricardo

I was elected Hobo King last year. You aren't making decisions or hobo decrees or anything like that -- it's about respect. The whole thing started with a hobo convention back in 1896 because a bunch of vagrants were getting ticketed and hauled away, but if you were carrying a card as part of a union they couldn't haul you away. So, they got together and did that and elected a president. These days it's a king and a queen.

If you want to ride the rails, be careful. It's dangerous! There are crazy people out there. I'm still riding but I don't want my full name out there, just in case. You might cross paths with someone and you never know what they heard or where from. Then they meet you and put two and two together and you got problems.

I've been riding since 1973. I was 22. My first trip, me and my friends wanted to go down to Idaho to see Evel Knievel jump the Snake River Canyon. We got all split up going down there and while we were on the train Evel had to cancel the jump until next year because somebody said it was illegal, but from then on I was hooked on the trains.

This is all stuff I learned from the older guys who started riding in the '40s and '50s.

I became a fruit tramp. You'd follow the fruit-picking jobs around California. Back then you could ride without hiding because the train wanted you to pick fruit because half the time the train was the one hauling the fruit out. You could knock on the door of the caboose and they'd give you water in a jug with the train company logo on it.

This is all stuff I learned from the older guys, guys who started riding in the '40s and '50s. They'd tell you how to ride, where to pick strawberries. You wanted to stay away from corporate farms since they'd just drive you. Local farmers were decent and sometimes they'd give you a cabin in the orchard to stay in.

You have to be careful of the bull. That's railroad security. He's just doing his job. You keep a train between you and the bull, you'll be OK. I'm talking about when you're in train yards and you're running from one train to another. Long as there's a train in between you it's usually safe because the bull isn't going to jump a moving train to get you.

You want to travel light. I never rode with gloves but some people say they're essential. I carried a cast-iron fry pan because I like to eat and cast iron cooks good on an open fire.

You have to have water. That's a must. You can go a couple days without food but not without water.

In the '70s we had jungles -- those are places to camp -- and that was like our phone lines. You'd roll in there, sometimes there'd be a pot of coffee; people just leave stuff for the next person. I've only found one jungle in recent years out in California. Now people are staying under bridges more. I don't know why.

Used to be the rule of thumb was that you went into a jungle and if there was someone there, you asked them to use the fire. If they pulled out a match and handed it to you, that meant they wanted you to leave them alone and go off somewhere and start your own fire.

That's the difference between a tramp and a bum.

To take something, you have to bring something. If you got something you throw it in the stew, if you don't have anything you go out and gather wood and earn your keep. That's the difference between a tramp and a bum. I started out as a tramp and I'll always be a tramp, but that means when I'm traveling I'm working to make my way. Bums don't do nothing. Most of them are the guys you see locally, just hanging around town.

Just don't ride stupid. I drank back in the '70s and that was one of the most dangerous things I could possibly have done, going around those huge yards with all the moving trains. There are kids right now riding what they call "suicide." That's when you're in a train car with no floor. Just some purchase around the edges. You can't go to sleep. You got to hook your pack up. You got to stand the whole way just above those wheels. I don't think people realize how dangerous those wheels are. There are parts of the ride where metal shavings from the tracks will get peeled off and just shoot up like shrapnel. You can butcher a deer with that stuff.

You can go to jail if you get caught. Mostly they'll give you a fine and charge you with criminal trespassing, but if it's a train yard that's had a lot of problems with hobos they might put you in jail for a couple days to send a message. Or citizens will see you riding the trains and call ahead to the police because they think they're doing you a favor, like they're trying to save your life or something.

It's the freedom. That's what I love. But it's a full-time job too. I'm a white guy, but if you want to know prejudice put on a backpack and take a walk through a strange town. You can't do it as a vacation. You're out there riding and you have to come back to work and that's in your head the whole time and then it's not freedom anymore. So I took a break and worked for a while. The second I retired, get the backpack, let's go.

Hobo tips for riding the rails
Jason Hoffman/Thrillist

Connecticut Shorty

My father was a well-known hobo named Connecticut Slim. He hoboed 44 years and is buried in the Hobo Memorial Section of the Evergreen Cemetery located in Britt, Iowa. When I traveled to Britt in 1990 with my sister, NY Maggie, to bury our father, we met a lot of his hobo friends and have been attending the National Hobo Convention every year since. In 1992 several hobos in Britt asked me to run for queen. I ran and was elected. I'm considered a hobo historian and give cemetery tours of the Hobo Memorial Section every August.

I took my first freight train ride in June of 1993. I hopped on a Southern Pacific freight train in Dunsmuir, California, with Road Hog USA. Our ride was on the rear deck of a one-hole grainer (grain car). The hobos call this type of ride "ridin' the porch." In total I've ridden 5,000 miles on freight trains. I've never been afraid. Just excited to be having a free adventure.

It's best to ride on the rear of a freight to break the wind. There's no way to be real comfortable on a freight train. They're made of metal and are real noisy, not to mention dangerous. You must be alert for danger at all times. I usually sit on my backpack to help cushion the ride. When I roll out in my sleeping bag I just put up with the hard steel floor and listen to the rumbling along the rails. I usually don't sleep anyway -- I'm too excited and don't want to miss anything. On a "piggyback" I put my sleeping bag around myself and back up against a truck tire to help break the wind.

In total I've ridden 5,000 miles on freight trains. I've never been afraid.

The hardest part of riding freights is carrying everything you need. No matter how light you pack, the load does get heavy. Sometimes you have to walk a long way to get to the trains and/or out of the yards. Most trips also require some hitchhiking or public transportation.

I always carry water, wear good shoes, long pants, have insulated underwear with me (even in summer), have a windbreaker, glasses to protect my eyes, ear plugs to protect my ears, leather gloves with the fingers cut out, dry food, sleeping bag, tarp, extra socks, plus a few other items. I always wear black clothes and try to "catch out" at night because it's harder to be seen.I carry water in smaller bottles here and there to distribute the weight. I wear a vest with a lot of pockets to help with weight distribution. I always carry what I consider real necessary to survive in my vest pockets in case I lose my pack. The rest of the items go in my pack. I roll the sleeping bag and attach it to the bottom of my pack.

No glass! All should be unbreakable. Many times you toss your pack off the train before you get off. Also, I carry a few large trash bags to protect my gear in case of bad weather, and a poncho.

Hobo tips for riding the rails
Jason Hoffman/Thrillist

Frog

I was waiting on a train and this group of kids jumped me and beat the shit out of me. So, yeah, you want to be careful. This was way back in 1995. I had seen this group of kids wearing baseball uniforms and carrying bats and I figured they were taking a shortcut through the train yard on the way to practice I'd guess. They came along, cracked me in the back of the head, and when I came to I couldn't walk and there was a bone sticking out of my pant leg.

So there I am, stuck in Casselton, North Dakota, thinking I'm going to get killed on the tracks. Finally I was able to flag down a train inspector and he's yelling and screaming at me to move off the tracks and I'm pointing at my leg because it's obvious he can't hear me. He yells out to me, "I'll get some help!" Comes back with the paramedics and took me 30 miles east into Fargo to have what was to be my first of many surgeries because the bones in my right leg were shattered from my kneecap down to my toes. Those kids had taken everything I had, even my boots, and they wanted to make sure I wasn't coming after them.

I was 45 at the time, and I'd been riding since I was a teenager and that's the first and only time anything like that ever happened to me.

You can bring a flashlight, but I wouldn't myself because you'll end up babysitting people all the time.

I started out in Jacksonville, Florida. I was getting thrown off beaches and stuck in jail overnight because they wouldn't let you sleep on the beach down there. I was just hitchhiking all across the country. Anyway, the police in Jacksonville released me and told me to get out of town in 24 hours. I met this guy Pinky, and he says to me, "You ain't getting a ride out of here from anyone. You might as well just catch out." I'd never ridden a train before so I didn't know what the hell he was talking about.

So he asks if I want a beer and I did. He asks if I have any money, if I've got a job, I tell him no. "Well, just wait here and I'll get you something." He brought me back two 40-ouncers of beer. Two hours later, I'm following him to jump on a train. I had this little goddamn Boy Scout pack back then -- hell, I was just about 16 -- and I passed that up to him on the train and he says, "Hop on!" That train was a loader. The car was just this big, black car with the sides open. Carries junk and scrap, usually. I never slept the whole night. I was just amazed how easy it was not to have to beg for a ride. I wasn't cold or anything, but by the time we got to New Orleans the next day I was filthy as hell. Fell in love with it that night.

I got the name Frog because I'm from Canada and I had a habit of speaking French in my sleep. I used to go by the name Canadian Wetback but when I got busted and put in immigration jail for a few days they said I needed to get a different name, anything else, so Frog stuck.

Travel light, that's the first and foremost thing. Always keep your ears and eyes open. Just have a bedroll and maybe a change of clothes you can wrap up in your bedroll, and make sure the colors are dark so you can be somewhat disguised on the train. And if you're waiting in the jungle to catch it's easier to go undetected.

You can bring a flashlight, but I wouldn't myself because if you have one of those you'll end up babysitting people all the time.

I spent 31 years doing it, altogether. I was Hobo King in '97. But I had to retire back in 2001 when my leg got amputated. The right leg those kids crushed. Surgery after surgery and they just never could get it to heal right.

Sign up here for our daily Thrillist email, and get your fix of the best in food/drink/fun.

Peter Rugg is a freelance writer whose stories have appeared in Rolling Stone, Complex, Vice, and Popular Mechanics, among others. Follow his intermittent tweets @petermrugg.