[November 19, 2025] David and I were 16 when he decided to hop onto a train and head out West; to ride the rails. We had been infected by the cowboy spirit, “Head West, young man, head West.” Just before our junior year in high school, we were exploring the abandoned towns that lay far out into the “boondocks,” where no one traveled anymore.
But it was David who was hell-bent on leaving West Texas and heading out to become a real-life cowboy. All we knew about being a cowboy was what we saw on TV, and that was probably all wrong. David, however, was not to be discouraged. One early August day, before the first day of school, he disappeared. The police came to my house to ask about David and to see if I had any information on his whereabouts.
The police left soon after, but not before I mentioned that David had been talking about ‘riding the rails’ somewhere out West, where he could work on a ranch as a cowboy. The police officer, who was very intimidating to me, said, “Bad idea, kid.” What do I know? I’m just a kid. The problem was that David was also a kid.
Fast forward nearly a year, and one day, David shows up at my door. He was thinner, darker from working in the sun, and had a strange aura about him. He had visited his family but wanted to share with me the stories of hoboing, as he called it. During the Great Depression in the 1930s, he would have been called a “teen hobo” and would have found company with others like himself.
During the Great Depression, more than 250,000 teenagers lived on the road in America. Many traveled across the country by hopping trains, even though it was both dangerous and illegal. I knew it was against the law because my Dad worked on the local railroad and told me to stay away from the hobos. “They’re mostly thieves, who cannot be trusted,” he said.
Like those during the Depression, David was looking for a more adventurous life—one filled with freedom, camaraderie, misery, and loneliness. And that’s exactly what he found. He nearly died in New Mexico when some older hobos accused him of stealing food and beat him badly. In Arizona, he got a job on a ranch, but he broke his left arm and got a concussion after being thrown from a horse.
David survived. He did send home letters occasionally to let his family know he was okay. His location was revealed, and he was later found on a ranch by a local sheriff who arrested him. Somehow, he talked his way out of it. Freedom was what he wanted, and he would do almost anything to keep it. Work was scarce, and eventually David decided to go home and finish high school.
David’s yearning to ride the trains headed West was his dream. He did odd jobs for low pay, sometimes none at all, except for a place to sleep overnight and a meal. Once, he stayed in a hay barn for two months, and another time, in a transient home somewhere in southern California with itinerant farm laborers.
The road was an education about the ways of the real world, full of tough lessons: cold nights, brutal railroad police, the fear of being arrested, panhandling, ostracism by locals, days without a meal, and the dangers of losing one’s life by hopping trains.
What struck him most was the unfathomable loneliness of his life at the time. And it was often cold and miserable. Being young, one can only pay the price of that freedom if willing to make the sacrifices that David and all the teen hobos did, every day.
Was it a mistake for David to ride the rails? Listening to him talk about his adventures on the trains in the summer of 1969, I don’t think he would see it as a mistake. The lessons he learned might have been tough, but they were valuable. David was never the same after his adventure, and I honestly don’t blame him for changing.
Would David ride the rails again? Yes.
For more information about riding the rails, there’s a book by Errol Uys called “Riding the Rails: Teenagers on the Move During the Great Depression.” Uys’ website can be found here (link here).
————
Please read my books:
I had no idea that folks did this, ever. And apparently those who rode the rr rails were not all young men but also some women. Although with the women, I certainly would want to know why. I assume to leave an abusive father.
Good one, Gen. Satterfield. I don’t think this is a hobby (LOL) that I would take up, regardless of how old I am.
Very nicely said about ‘riding the rails.’
Sir, I had no idea that so many teenagers were ‘riding the rails’ in America. That probably doesn’t happen as much today, given our economic condition; which is darn good, at least compared to the Great Depression era. Also, our kids today are darn soft mentally and physically. They would rather be glued to their phones than doing something that required patience and endurance and resilience. Thanks for this article on something I knew nothing about and for the lessons we can learn from it.
How was David different? I wish Gen. S. had specified how he was different, other than having a dark tan.
Growing up in the 1980s, I heard of this before but only by “vagrants” and “mentally ill” persons. I didn’t hear about teenagers or “normal” people riding the railroad cars to wherever it might be going. Is there adventure in that? This quesiton is at the heart of what Gen. Satterfield wrote. I would vote ‘yes’ as an answer but I would hesitate. Courage is certainly a part of the adventure of riding the rails, like much of any extreme sport (a topic Gen. Satterfield used to write about). I believe the answer is indeed there is excitement and not to mistaken for an adventure.
Interesting take: “Would David ride the rails again? Yes.”
Something new every day from the brain of Gen. S. Sir, Thanks!!!!!!!
Ernest, yep, that’s why we are regular fans of Gen. Satterfield and his leadership website. It’s been more than a decade since he started his website/blog and I’m one of the early fans. There has been an evolution in his thinking and focus of this site he put together, and I like the way he is giving us both theoretical but proven advice (so maybe it’s not theoretical) and examples of how to be a good person. Don’t be fooled b y the other so-called leadership websites that are after your money. This site is free and he says it will remain so. But please get a copy of his books:
“Our Longest Year in Iraq”
“55 Rules for a Good Life”
You can’t go wrong. Look up the reviews and you’ll see the books are both highly rated, and they are inexpensive. So no reason not to get yourself a copy.
Thanks, Yusuf for the confidence in my site.
Gen. Satterfield, indeed, it just might take some real courage to “ride the rails” with the danger of falling off or getting crushed in a switching yard. I can understand why the RRs had RR police, as to insure no one got themselves in such a tragedy. Plus the RR police prevented theft. I’m not sure if they have any police any longer or if that responsibility reverts to a local jurisdiction. Good article on a rare subject.
I had no idea there was such a thing as riding the railroad rails.