A Professor Takes to the Rails

Cliff Williams (Oats)

Not long after I started going to the National Hobo Convention in Britt, Iowa, in 1990, I began to wonder what it would be like to ride a freight train. By the fourth year, I had to know. I bought a one-way Amtrak ticket to a small town in south central Iowa that wanted some hoboes and hobo-types on hand to help them celebrate their sesquicentennial. By then, I figured that I could play the part of a hobo-type.

Luther the Jet happened to be at the celebration and was planning on traveling by freight train to Chicago, near where I lived.

“Can I come along?” I asked.

“Sure,” he replied.

We caught a train when it stopped to change its conductor and engineer, hopped off when the train pulled into a yard halfway to our destination, then for the rest of the way rode another train that had stopped to pick up cars.

Ever since that first ride, I had to go again and again. Perhaps it was the adventure. Maybe it was the awe-evoking largeness of the train cars or the excitement of doing something totally different. Whatever it was, I ended up going several dozen times over a dozen or so years, racking up a little over ten thousand miles. That may seem like a lot, but it was not much compared to real hoboes who rode between ten and twenty thousand a year.

Mostly I went alone, but sometimes I went with other trainriding acquaintances I had picked up—Milwaukee Mike, Leo, Collinwood Kid, Socx. Once I found myself with Train Doc, Shoefly Jay, and Brakeshoe in a boxcar heading south along the Mississippi River at dusk. At times we were so close to the river that we could just about jump into it. Its wide expanse divided the dim, dark mass of the opposite shore from the shadowy trees and bushes that rushed past us.

Shoefly Jay, Brakeshoe, Oats

Alone I lay on the porch of a graincar or in the well of a doublestack gazing at the Milky Way. The rush of wind penetrating my sleeping bag kept sound sleep at bay. Sometimes, though, I slept through the crashing of cars and the squealing of brakes. When I woke up I didn’t know where I was. No one else knew either. Something about that felt exhilarating.

Usually I knew where the train was going because of information I had gotten from other trainriders. Once, though, I ended up in Grand Rapids, Michigan, when I wanted to go to Minneapolis. Most of the time I planned my trips some days in advance.

One Friday, however, as I was heading up the stairs to my office, a sudden urge to go somewhere that night took hold of me. I taught my classes, held office hours, went home, ate supper and got my gear together, then headed for a railroad yard and caught a train going west. I wasn’t too sure that day whether I was a college professor with a secret life or a trainrider masquerading as a college professor.

There is no doubt that riding the rails is romantic. You see things you could never see by car or plane. You are one with the moving, swaying train car. The wind blows in your face. You have done something few others do.

The romance wears off, though, when it starts to rain and you shiver. It withers when you get tired of screeching and crashing cars, or when you ride in the blazing sun and fear you will get heatstroke. It pales into debilitating boredom when you have to wait a day or two for a ride.

By riding trains, I found out a little bit of what it is like to be a hobo. I felt the peace and calm of being completely alone. I encountered in a stark and dangerous way a force that I could not control. I went to out-of-the-way places. I was my own person. I felt as if I was back home again whenever I got on a train. I sat under dark bridges and hid in bushes. I felt wild and free.

I did these things even though by day I was entrenched in “normal” culture. Except for a few acquaintances here and there, no one in my regular world knew that I made forays into subterranean territory. To them, I was a respectable college professor.

I remained one until 2018. During the last few decades of my fifty years of teaching, I found that you can experience romance and be your own person even though you are not out roaming the rails. You are, to be sure, limited by social realities, but you are also limited when you are hiding in tall weeds or under bridges. The truth is that you can find as much romance in one as in the other. You do not need grand adventures to get it. You can get it in the thousand and one settings you find yourself in during a single day.


P.S. If you are tempted to try riding a freight train for yourself, read this warning from Nomad, a veteran railrider: “Do not do what I do. It is dangerous. It could get you killed. It’s illegal—you can go to jail. And you’re going to get addicted to it and possibly destroy whatever chance you could have at a real life.”

Discover the romance of life in a different way.


About Cliff Williams

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