The Ultimate Road Trip

And you don’t have to cut the grass: Make your bed the backseat and this is the view out your living room window.

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. Seems like, to me, if you’re going to have any sort of grand epiphany, it’s not going to come while you’re sipping mimosas at the Four Seasons or getting a hot stone massage.

Which is pretty much why I was standing on a sidewalk in Astoria one Tuesday morning last October, not asking myself why I was there at all. I just stared at a newspaper box in front of the Columbia River Coffee Roaster, under the concrete and steel of the south end of the three-and-a-half mile long Astoria-Megler Bridge spanning the mouth of the river, and scratched my chin reading the Daily Astorian headline: “Protestors Occupy Seaside.” If the Occupy Movement was in Seaside, a little 6,500-person town on the Oregon coast, it was everywhere. It was October 11th, and in less than a month, I had watched it spread from Wall Street to places like L.A., San Francisco, Portland, my hometown of Denver and Seaside.

When I’m older, the Occupy Movement is what I’m going to remember was going on while I was living nowhere. The way people can tell you where they were when they heard about the 9/11 attacks, or the Kennedy assassination. I’ll frame the best and worst time of my life, this road trip, with Occupy Wall Street and everywhere else… I was occupying no place. And sometimes it was a little uncomfortable.

Like the previous night.


I had parked at a rest area just on the Washington side of the Astoria-Megler Bridge, trying to sleep in the back of my car. The wind blew hard off the bay, rocking my Subaru in the driving rain. I couldn’t sleep, my body wedged into a Z shape in the back, crunched because the car was about eight inches too short for me to stretch out. Why did I decide to sleep here tonight, I asked myself at 1:00 a.m. I didn’t feel like setting up a tent in the rain, and I had to be online for a 9:00 a.m. conference call the next morning with a corporate client. That’s why. But not exactly why, I guess.

October 10 marked 10 weeks of living in my car, since the start of my trip, five weeks of climbing followed by five weeks of working from the road, sleeping in a new place every night, finding wireless Internet in coffee shops, libraries, the occasional McDonald’s. In less than two-and-a-half months, I had slept in 33 different places in Colorado, Wyoming, Idaho, Utah, Montana, Washington, Oregon, California. This would go on for several more months, although I didn’t know it at the time.

I had left Denver on the last day of June, exactly a month after she and I broke up. I gave up on marrying her. We split up our stuff, moved out of our apartment, gave the keys back, and I thought I’d get in some good thinking time out on the road. Figure out what was next for me.

When your life plan explodes, you ask yourself big questions. You want a clear answer, and maybe the answer doesn’t come all at once, but over several experiences, a dozen conversations, a few thousand miles, a glimpse into a few dozen lives. The ocean, the mountains, the stillness that comes with a couple hours of driving, sunsets, sunrises, the unease of not knowing where you’re going to sleep each night. To me, there was nothing more American than hopping in my car and taking off to drive Out West, hoping something big, something life-altering, something that would make sense of my life, would happen.

At 32, I had no mortgage, no car payment, no kids, no pets, no plants and when my relationship ended, I had nothing keeping me in Denver. I was a dirtbag. I would take off and see the country, just like Kerouac, just like Steinbeck. The open road. It would be nothing short of magical. Right?

When I got a job as a remote copywriter the year before, people said, “That’s great, you can work from anywhere.” But I didn’t. I just worked from my kitchen, and a couple coffee shops near my apartment. Then, when the aforementioned big breakup happened, I moved out of our apartment, and now I was doing it, working from anywhere. Waking up in my car, nodding hello to the guy collecting the trash outside the rest area bathroom, then driving into Astoria to sit on a conference call from a coffee shop under the shadow of that magnificent bridge. That afternoon, I planned to drive south, camp along the coast, and find a new “office” the next morning. Start making my way to find some sunshine in California somewhere and see some friends.

Trunk living

If my dad and I didn’t understand each other as well as we do, he might have said something like “What the hell are you doing that for?” when I told him what I was doing the night the St. Louis Cardinals won the pennant. But he didn’t. I called him a few seconds after the Cardinals made the final out in Game 6 of the National League Championship Series, as Cardinal fans pumped their fists and screamed and jumped up and down in bars and living rooms across the country, and he narrated the scene he was watching on his living room TV in Iowa. He said, “Where are you?” I said, “I’m in my sleeping bag in the back of my Subaru at a pullout on this ocean cliff near Newport, Oregon,” and he said, “Great. Yeah, everybody’s rushing the field now. What a game.”

Off I-15 in southern California, a few miles down Cima Road, on a dusty asphalt two-lane that cuts through the middle of the lonely Mojave National Preserve, there is a strip of desert that should be famous. The Shadow Valley is one of the densest Joshua tree forests on the planet, a still army of gnarled yucca branches like something out of a Tim Burton movie lining the sides of Cima Road as far as you can see in both directions. I drove through at sunset, when the sun is so low in the sky that everything in the world is painted half-gold and you love it no matter what it is. Traffic is so sparse here, I could have sat down on the dotted yellow line in the middle of the road and shot photos. But I wanted to find a campsite before it got dark.

A half-mile downhill from the turnoff, my cell signal suddenly disappeared. I pulled off the asphalt in front of a granite dome, slowly drove around the back on a dirt road, and parked, out of sight of the half-dozen or so cars that would drive by during the night. I rolled out my sleeping bag right in front of my car, cooked dinner, flipped open my laptop and started to write under the light of the stars. This was the good shit, what I was after, the vision of what I wanted to do on this trip. When I talked to some of my friends on the phone, this is what they imagined I was doing when they said words like “jealous,” “adventure,” “envious,” and “living it.” If they saw me working on my laptop in a Starbucks next to a truck stop off I-10 the next day in Barstow, they wouldn’t be so envious. That evened things out a little.

I didn’t have a home to go home to, no furniture, no lawnmower, no big TV to spend my Sunday afternoons in front of when I got back. Some days I had a little doubt about what was going on in my life. I looked up the trade-in value of my car one day, and it was $650. And I was living in it, sleeping next to about $1,300 worth of climbing gear in a Rubbermaid container. I had a master’s degree. I had a good job.

I was totally failing at the American Dream of stability, home ownership, a reliable car, or just having a mailbox for my credit card bills. Wasn’t I? Most days, it was pretty good. I got behind the steering wheel, started out for someplace new, the world opened up in front of my windshield, I turned the music up, and I had these little epiphanies, pieces of essays that I scrambled to write on scraps of paper on my steering wheel, trying to get it down on paper and not hit the semi in the next lane.

I had been pretty irresponsible for a young professional, leaving the paltry salary of a newspaper gig for the barely-surviving salary of a nonprofit job when I was 29. I had never saved much money, certainly not enough for a down payment on a house. I listened to people say, “You’re throwing your money away paying rent,” and they were right. My palms got sweaty at the thought of owning a home, being responsible for all the things that could break in a house. What if the water heater went out and I had to cancel a climbing trip to pay for a replacement? So I kept renting, calling the landlord to fix things when they broke, and spending my weekends climbing.

Then the housing market crashed. Then the economy. Then I heard friends say things like “We’re going to move, but we can’t sell the house till the market recovers.” Other friends turned down promotions because they couldn’t sell their house so they could relocate. Or they said “We’re just hoping to break even on the old house before we move into the new one.”

Being irresponsible put me in a position to hit the road when things went nuclear for me. I wasn’t tied down to a house or a condo or a mortgage. I could cut and run. From my rearview mirror, I started to look at our traditional idea of The American Dream and wonder if it was the opposite of freedom.

Enlightened desolation: As Kerouac said: “There was nowhere to go but everywhere, so just keep on rolling under the stars.”

Freedom for me became pulling into a campground on the Oregon coast, or in a Montana canyon, or next to a shoreline cove in Northern California, rolling out my sleeping bag, making a simple dinner and getting eight hours of that not-so-good-but-good-in-a-different-way sleep you get on the ground. In the morning, I’d eat a bowl of oatmeal, brush my teeth in the open air, or the light rain and watch seagulls hover over the water or a morning breeze blow through pine trees, and then I’d go find my “office” for the day. I slept in my sleeping bag so many nights, under the stars, out in the open air, no thermostat on the wall, no walls at all, and I didn’t know what I was doing, but it felt like I was doing something, maybe the right thing, or at least way more right than moping around a now-half-empty house in Denver and wondering what was going to happen to me.

In his circumnavigation of the Lower 48 in Travels With Charley, John Steinbeck kept meeting people who saw what he was doing, and wanted to do it with him, or like him, but were too tied down to houses, jobs, whatever they considered “roots” somewhere. People just wanted to go. They wanted to see about this myth of the freedom of the open road, see what was out there. And maybe many of us still do. Steinbeck set out in 1960 in search of America. My generation? If we go, I think most of us are hitting the road in search of ourselves.

Twenty-some pages into Travels With Charley, Steinbeck stops his camper-truck to get some liquor for his 10,000-mile journey, and the liquor store owner helps him carry a box of bottles out to the truck. When the liquor store owner sees the truck, Steinbeck says he saw “a look of longing” on the man’s face. He said to Steinbeck:

“Lord! I wish I could go.”

“Don’t you like it here?” Steinbeck asked.

“Sure. It’s all right, but I wish I could go.”

“You don’t even know where I’m going.”

“I don’t care. I’d like to go anywhere.”

It was so different now than when Steinbeck did it, wasn’t it? But it was so the same, too.

My phone rang just north of Bandon, Oregon, on the coast. My friend Aaron asked,

“How’s your trip going?”

I said, “Well, it’s kind of just become my life now, I guess, and not so much a trip anymore.”

You know what you do at the end of a trip? You go home. You go back to all the things you missed while you were away, whether it was your husband, wife, kids or just your bed. You put your toothbrush back in the bathroom cabinet where it belongs and you sigh and you get grounded again.

So what if you left on a trip and there was no home to go back to? It looked something like what I was doing.

Aaron said “I’m envious of what you’re doing,” and I said, “It’s nothing too fancy, just some dude living in his car, driving around.”

He said, “I’m jealous, man.”

I said, “Remember that when you’re spooning your wife in a nice warm bed and you can get up and make a sandwich whenever you want, and I’m out here crammed in my car, eating macaroni and cheese at some campground and talking to myself.”

Aaron just laughed.

Brendan Leonard is living nowhere for a year. Portions of this essay appear in his yet-to-be-published book project, The New American Road Trip Mixtape.


Find even more guides and stories under our Travel Section!

Previous articleKeep it Light
Next articleNuts and Bolt

Related Stories


The All-New Looper MIPS Helmet

Sweet Protection is based in Norway and was founded by a tight-knit group of skiers, riders, cyclists and paddlers, looking to make...

The 5 Things You Need to Do in Durango this Winter

Winter is in full-effect in southwestern Colorado!  For those seeking freedom from the couch, Netflix,...

Local Goods | Wilderness Sports

Before hitting the resort or heading into the backcountry this season, you need to be equipped and ready. This legendary shop has...

Bentgate’s Holiday Gift Guide

reVessel: Adventure Kit | $124.95 Leak Proof Lid, Built in Cutting Board, Toxin-Free