The Story Of When I Hitchhiked Across The Country By Plane

Pictured: my dad tracing the route of that first Laramie-to-Chicago flight on his old Times Atlas of the World. Piper Cherokee D, a popular plane of the era, for illustration.
Pictured: my dad tracing the route of that first Laramie-to-Chicago flight on his old Times Atlas of the World. Piper Cherokee D, a popular plane of the era, for illustration.

You asked me about the times I hitchhiked by private plane, and I’ve been thinking about it a lot. It was a long time ago, and it is a story that I don’t tell very often. It’s as if the beginning of the story is the best part—I once hitchhiked by private plane—and then it’s downhill from there. So it’s been good to think about this, to recall the details, and to piece it back together.


(Welcome to Jalopnik Father’s Day, where we are celebrating the wonderful dads of the Jalopnik staff. This is a story from Ben Orlove, dad of Jalopnik features editor, Raphael Orlove.)

I’m quite certain that the first time I hitchhiked by private plane was during my junior year in college, when I was much further west than I’d ever been, except for one trip when I was two years old, from which I remember nothing except a basket of kittens under the kitchen table of some friends of my parents.

This was a trip during spring break after the summer when I went to Europe on a cheap ticket with Icelandic Airlines and traveled with rail pass and stayed in youth hostels, except for the time which I spent a night in a squat in Copenhagen. That’s another story that I don’t tell very often, because its opening line is so much better than the rest of the story.

I met a number of people that summer, very different from my friends from my old neighborhood in Brooklyn and from college. Among them was a girl named Terry, who was, I’m not making this up, the daughter of the sheriff in Laramie, Wyoming. I wonder if I would’ve had the courage to talk to her for a long time if I hadn’t quickly learned that she had a boyfriend. But we really hit it off, with all the other people in the youth hostel in Amsterdam, and we corresponded—as people did, back then before the internet. So she and I agreed that I could come out and visit her during spring break. I stayed with her family, who had an apartment in the building that also held the county jail. This was a low-key jail. No one was in for very long. Terry’s mom would bake pies for the prisoners if she felt sorry for them.

The trip to Wyoming was really unpleasant. I found a note on a ride board—something we had back then, just pieces of paper with the dates and destinations scribbled on them and loosely organized by region. The guy who was driving out west sounded good because he was heading through Wyoming and was traveling quickly. And he didn’t mind that I didn’t know how to drive.

Turns out that he didn’t want to talk at all, but just wanted someone to sit next to him. So there were just a few long, silent days and nights in cheap motels until we got to Laramie.


The stay in Wyoming was fun, even though I have the sense that Terry’s boyfriend Barry didn’t really care for me. We all went to her parents’ cabin and hung out a lot in town. (I did later visit Terry and Barry when they were in the Peace Corps in Venezuela, in the tiny town on the Orinoco. That’s the place where I ate mangoes in the river, if you know that story.)

Eventually, it was time for me to head back to college. I hadn’t really planned how to get there. The ‘60s were not a great decade for planning. And on a whim I headed to the airport. It wasn’t far out of town at all. I got there in the morning, and walked out to where the private planes were. I kind of remember a big open field, with a few small planes, and some mountains in the background. It was early in the morning, I’m pretty sure I stood out in the field for a while, and then went into the building, and when someone walked in I just asked if he was going east. I asked if he could take me, and he said sure.


What I mostly remember from the flight can’t be true, because it seems to me that we spent many hours flying at an elevation of about 200 feet. But I’m sure that we did fly low enough for the prairie to seem close, and to seem immense and fascinating. I have flown over the Sahara, and it does have long trackless sections. I can just summon up a few images from that flight out of Laramie, which was not so bare. The grasslands and farms were varied enough, seen from my vantage right next to the pilot, to hold my attention. I think I had found a second silent driver. But this one offered me a better view, and was moving much faster.

We did eventually get to Chicago, where he left me at the terminal. I must have had the phone number of one of my old high school friends who was in college there, because after a bit, a carload of people arrived to greet me. I stayed with them for a few days, and everyone agreed that it was a pretty cool thing, what I had done.


So when was the second time that I hitchhiked by private plane? I know I’ve done it twice, because I felt there were some things that I learned on my first trip that I applied to the second. I don’t recall exactly how I got back from Chicago, but I don’t think it was by plane. Most likely I took the bus.

The second time, I’m now really quite sure, was a shorter trip, from Boston back to my parents’ home in New York. I remember going out to the section of some airport where the private planes were. And I remember being very smug about my cleverness in hitching a ride. This time, instead of asking right off the bat whether someone could take me, I asked a series of questions:

“Where are you going?”

“Is your plane full?”

“Oh, so you have an empty seat? Could you take me?”

The first two people who I tried my brilliant scheme on didn’t offer me a ride, or maybe it was three. But I did get to sit in the second row of a slightly larger plane, all the way to New York. I remember the different, and much more varied, New England scenery below us. But mostly I remember the pilot—a doctor, who had this plane as a hobby—and the person next to him, his father, up in his son’s plane for the first time. The son so clearly wanted to impress his father. Of the doubtless numerous comments of the father that infuriated the son, I can only remember two: the father pointing out that another plane, visible not very far away, was larger than the son’s, and his indicating a cloud somewhere off in the distance that he felt he had to tell his son not to fly into. I’ve wondered whether it was fortunate that I was there with them, to prevent the son from committing some act of violence against his father, likely causing the plane to crash.


This story appears unedited except for fixes to spelling and grammar, as recounted by my dad into his phone. I brought up with my mom (who was not present for this adventure) that I was getting this story for Jalopnik. “Ah yes,” she said, explaining a more succinct version of the events: “It was the ‘60s.” -Ed.



This is actually quite brilliant.

When I was doing flight training a lot of the time I was just cruising around on my own. If someone was at the airport and asked for a ride I wouldn’t even think twice about saying hop in.

I bet it would still work in some places.