Get inspired to take the Great American Road Trip

road trip

Writer Brendan Leonard sits outside the Refuge Sorellier writing in his notebook while on a climbing trip to the Aiguille Dibona. Photo by Dan Patitucci

The Great American Road Trip is a dream for many, a reality for few. At 32 years old, a little world-weary and still aching from a recent breakup, Brendan Leonard decided to embark on his own cross-country odyssey on a search for answers to the questions everyone ponders at some point: "What do I really need in life? How can I make my life a work of art? What is a life?”

Leonard has immortalized his real-life story in the new book “The New American Road Trip Mixtape,” an honest and absorbing examination of one man's journey to uncover his own version of the "American Dream." We caught up with Leonard to talk about the stories that inspired his trip, his advice for hitting the road, and the ultimate road trip anthem.

We love that you gave a girl a copy of “On the Road” to get her to date you--genius. What is it about road trip literature that you love most?

I think the idea of possibility, or opportunity, in the stories, but also the accessibility of the characters. Joseph Campbell mapped the “hero’s journey” nature of many of the stories we love, and in road trip stories, the hero is often someone like you and me: a person who’s trying to figure it out. If you’re struggling to find meaning and you read “On The Road,” “Travels With Charley,” “Blue Highways,” “Zen and the Art of Motorcycle Maintenance,” or other classic road trip books, it doesn’t seem like something you can’t do--I mean hell, I own a car, why can’t I go on a soul-searching road trip? And of course you can. You may not write the next “On The Road” or “Travels With Charley,” but you can find some answers.

Do you think the notion of the “American Dream” is changing?

I think the family model is changing and our view of consumerism is changing and that makes people less focused on the status quo. I have so many friends who are single parents, or have families with adopted children, or have children from a previous marriage, or decided to not have kids or just one kid, and everyone seems less caught up in this image of a “perfect home” with a mom and a dad and two kids and brand-new matching appliances and a trimmed lawn. They’re more focused on their own version of happiness and getting by, even if it’s a little complicated when you look at their family tree.

Living on the road just feels so romantic, but I think we both know there are downsides. What do you miss most?

I’m still living on the road, two-and-a-half years after the narrative that begins “The New American Road Trip Mixtape,” so I’m pretty familiar with the downsides. I’d love to shower more frequently, I suppose, and I get a little tired of loitering at coffee shops and libraries because I have nowhere else to work, and it’s kind of difficult to be healthy--but any complaints I have fall away when I consider stopping doing what I’m doing.

So what are the moments that make you feel like living our of your car is worth the infrequent showering?

I am grateful for the number of sunsets and sunrises I get to see, whether through the windshield while driving to the next place, or out the back window of the van when I wake up somewhere different. What I do is far from a vacation--it’s more like running a business that’s completely mobile and dealing with all the pros and cons of that--but I never lose sight of the excitement of being able to flip my laptop closed and pick up and leave at the end of every workday, and head to Moab or Jackson or Joshua Tree or wherever happens to sound good.

Why did you decide to immortalize your experience in a book?

I think the first three months of living on the road felt like something was happening, whatever I was doing--things people said to me, things that happened while I was driving around the West, conversations I had with friends--felt like a story when I was living it. The reason I wrote it is because I hope the story might help people--inspire them, get them to take a step back and think more about what’s best for them, help them dream, help them pack their shit in a car and go find a story to tell their grandkids someday, whatever. If I’m dealing with some questions, someone else out there might be too, and maybe a story I write can help them deal with it.

The New American Road Trip Mixtape by Brendan Leonard

The New American Road Trip Mixtape by Brendan Leonard

What advice do you have for someone who wants to do something similar to what you did?

Go do it, whether it’s a week or a year. Go see the friends you are always talking about visiting “someday,” and go see all the stuff you’ve wanted to see, whether it’s the Tetons or the world’s largest ball of string. Drive until you find a spot where you don’t get a cell phone signal, and spend a day or three poking around all the towns and cities and wild places you always wondered about. And don’t plan every minute of it. If things don’t go as planned, it’s stressful. If you have no plan, things can’t really not go as planned. And then it’s a trip, not a to-do list. Also, when you’re done packing your car and you’re ready to hit the road, go through your stuff one more time and get rid of at least 12 clothing items.

We have to ask--what songs were on your driving mixtape? What is your ultimate road trip anthem?

When I hit the road, I had 740 songs on my phone, and I of course bought tons more as I was driving. There’s a chapter that starts with a discussion of road trip music and how much you need, and it includes a list of what I consider the top five road trip songs of all time. (I won’t tell you what they are, but it’s Chapter 6 if you read the book.) I listen to a ton of old hip-hop, but it’s not what I consider driving music. If you’re on a soul-searching drive, I think you need every The National album, Gregory Alan Isakov, Willie Nelson, Paul Simon, My Morning Jacket, Andrew Bird, Devendra Banhart, and of course lots of Bob Dylan, including “Blood On The Tracks.”

Midway through the trip that’s the narrative of “The New American Road Trip Mixtape,” my friend Drew introduced me to this song “The Stranger” by a band called Lord Huron, who only had a four-song EP out at the time (late 2011). If you want to call something a road trip anthem, that would be mine. That’s the song I hear when I think of those months I spent driving by myself, a little sad, and little lonely, watching the ocean roll up on the cliffs in Oregon and California, and all those desert sunsets I saw by myself through the cracked windshield.

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