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Re-Dreaming the Great American Road Trip

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Author Brendan Leonard; Photograph by Forest Woodward

When I was 17, I read On the Road and idolized Jack Kerouac’s narrator Sal Paradise and his pal Dean Moriarty, the Kings of the Open Road. Beyond the flat cornfield horizon of my hometown in the corner of northeast Iowa, there was more flat cornfield horizon in all directions, but beyond that was something, I thought. If I escaped someday, maybe I could find something like Sal and Dean found out there on their trans-America road trips.

One morning when I was 32, I woke up in the back of my Subaru wagon at a rest area on the Washington side of the Astoria-Megler Bridge at the mouth of the Columbia River. I had crammed five feet and 11 inches of me into about 5 feet 7 inches of space the night before, intermittently sleeping on one side, then the other, waking up every time the wind rocked the car or another blast of rain hammered the roof. The storm passed, the sun cut through low clouds, and I worked my way out the rear passenger door, toothbrush in my mouth. I walked across the rest area parking lot, nodding to the guy changing the trash as I walked into the restroom.

I had been living in my car for ten weeks, bouncing around eight states, sleeping in 30-plus different places in a trip that started with a breakup and had taken on an indefinite and increasingly hazy end date. The previous night, I had closed down the McDonald’s in Astoria, typing on my laptop at a booth in the back and nursing a small coffee at the only place with public Wi-Fi. It was not quite a scene from On the Road, but hey, you know, sometimes dreams can come true. Even if you don’t feel like it after the third time you’ve brushed your teeth in a public restroom.

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Finally, at 32, I was doing the Grand Tour, the big trip where I got to figure things out, search out life (or something) like Sal and Dean. It was great and lonely and eye-opening and sad and fun. I stopped by to see friends in Wyoming, Montana, Washington, Oregon, California, and Arizona, and we did nothing special sometimes but it was way better than liking their photos on Facebook or sending a twice-a-year e-mail. Some weeks, I just drove around by myself, not getting enough conversation with other people but instead getting an abundance of sunsets, sunrises, and time to ponder while staring out the windshield.

Why do we think this is a good idea? We: Americans. Life kicks you in the stomach, so you take off to hit the road, instead of hitting your neighborhood pub or some therapy? There was something to that.

I bought my first copy of John Steinbeck’s Travels with Charley at Fact & Fiction in Missoula, Montana. I re-read On the Road. I made a list: Blue Highways. Zen and the Art of Motorcycle Maintenance. Into the Wild. Fandango. Thelma & Louise. Tangled Up in Blue. Ramblin’ Man. On the Road Again. American culture is rife with mythology about the road as a place to find answers. But does anybody believe it anymore?

This guy in his early 30s driving around in a beat-up station wagon sure did. I started writing, flipping open my laptop at campsites in the Mojave Desert and next to the Pacific Ocean, in coffee shops, libraries, and laundromats. Sometimes I dug through my car as I drove down the highway and pulled scraps of paper, tickets, receipts, napkins, and scrawled sloppy notes and phrases as I steered with a knee, using the middle of the steering wheel as a desk. I wrote things like:
I don’t know if I’m the only one who thinks that when you set out looking for the big answers in life, you gotta be as uncomfortable as possible when you do it. 

Is there such a thing as a “comfortable bed,” or is that just a feeling we have when we’re at peace enough to sleep at night? 

If you could live anywhere, wouldn’t you want to live everywhere?

We find inspiration in those books and movies and songs, but not quite the answers. The answers are still out there somewhere, on the highway.

The New American Road Trip Mixtape is available in paperback and ebook formats at