The List: The 9 Best Road Trip Books

If you take off on a road trip and you call it a road trip, you do it at least

If you take off on a road trip and you call it a road trip, you do it at least partly because of the American mythology of road trips — because someone wrote a song, or a book, or a screenplay that said a journey would bring adventure, or romance, or clarity, or all three. Writing good road trip books could almost be called an American tradition: turning a long drive into a story that’s true art.

1. On the Road by Jack Kerouac
Maybe the most legendary of road trip books, Kerouac wrote the first draft of On the Road over 11 days in 1951 on scrolls teletype paper cycling through his typewriter (and later taped them together to form a 120-foot scroll, above). Six years later, the autobiographical story of Kerouac’s ramblings (as Sal Paradise) across the country with Dean Moriarty was published and became an American classic and vaulted Kerouac to literary fame.

Quote: “What did it matter? I was a young writer and I wanted to take off. Somewhere along the line I knew there’d be girls, visions, everything; somewhere along the line the pearl would be handed to me.”

2. Travels with Charley: In Search of America by John Steinbeck
Steinbeck set out in a custom-made camper-truck, which he named Rocinante (after Don Quixote’s horse), in middle age — he was 58, married, and well established as a writer. He wrote that he wanted to get to know the America that he’d made his living writing about, and he did, with mixed results. He wanders across the country, meeting people of all backgrounds, some of whom just want to join him for a while, on the road, and he wonders, “Perhaps we have overrated roots as a psychic need.”

Quote: “A journey is a person in itself; no two are alike. And all plans, safeguards, policing, and coercion are fruitless. We find after years of struggle that we do not take a trip; a trip takes us.”

3. Zen and the Art of Motorcycle Maintenance by Robert Pirsig
With a Guinness World Record-setting 121 rejections, Zen and the Art of Motorcycle Maintenance was a longshot to become a bestseller – but it did, selling five million copies worldwide, landing on reading lists for business schools, and spawning one gazillion references to its title on the internet (Zen and the Art of Central Banking, Zen and the Art of Landscaping, Zen and the Art of Poker, ad nauseam). Not bad for a novel that is indeed about philosophy (and the concept of quality) and keeping a motorcycle tuned, tagging along on a narrative of a 17-day road trip from Minnesota to California. Those who love it love its insight and the duality of subject matter, and those who don’t sometimes call it “unreadable.”

Quote: “Sometimes it’s a little better to travel than to arrive.”

4. Blue Highways: A Journey into America by William Least Heat Moon
When he lost his job and split with his wife at age 38, William Least Heat Moon did what every one of us think we should do: Hit the road. Moon stuck to what he called “blue highways” – the often-neglected non-interstate highways that used to be colored blue in the Rand McNally Road Atlas. The result was 13,000 miles of soul-searching across rural America in his van named “Ghost Dancing,” which is now in the Museum of Anthropology at the University of Missouri.

Quote: “What you’ve done become the judge of what you’re going to do – especially in other people’s mind. When you’re traveling, you are what you are right there and then. People don’t have your past to hold against you. No yesterdays on the road.”

5. The Electric Kool-Aid Acid Test by Tom Wolfe
Neal Cassady (the inspiration behind Kerouac’s Dean Moriarty in On the Road) drives Ken Kesey and the Merry Pranksters’ day-glo painted school bus, Furthur, in a psychedelic-drug-fueled trip across an America that may not have been quite ready for it yet. As if it needed more color, Tom Wolfe documented it all and brought it to readers in his high-energy style of new journalism.

Quote: “Everybody, everybody everywhere, has his own movie going, his own scenario, and everybody is acting his movie out like mad, only most people don’t know that is what they’re trapped by, their little script.”

6. The Lost Continent: Travels in Small-Town America by Bill Bryson
Perhaps only Bill Bryson can turn such aimless wandering into a great travel book – beginning in his hometown of Des Moines, Iowa, and searching for an idyllic small town, which he doesn’t find, but gains an understanding of rural America. Perhaps equally hated as it is loved by readers, Bryson observes, reports, contemplates and mocks America, and Americans, in a journey covering 42 states.

Quote: “I mused for a few moments on the question of which was worse, to lead a life so boring that you are easily enchanted, or a life so full of stimulus that you are easily bored.”

7. Honorable Mention: Fear and Loathing in Las Vegas by Hunter S. Thompson
“Buy the ticket, take the ride.” Thompson’s wacky, wonderful and depraved tale of a trip to Vegas with his attorney, loved by many, and imitated by many more.

8. Honorable Mention: Killing Yourself to Live by Chuck Klosterman
Music and culture writer Klosterman explores death in American music around the country in a 6,557-mile trip, from the field where Buddy Holly’s plane crashed to the Mud River where Jeff Buckley drowned.

9. Honorable Mention: The Odyssey by Homer
Not American. But before you call your road trip “epic,” please consider.


Brendan Leonard is a contributing editor to Adventure Journal. Follow him at his blog, Semi-Rad.
Showing 23 comments
  • Keith G

    Why not make it 10, and add Jean Beaudrillard’s “America” to the list. He’s not American, but he certainly captured something of America that maybe is less visible to Americans in this book. It’s a provocative read.

  • Andy

    Ugh. Can we please just be done with Zen and the Art of Motorcycle Maintenance? I understand that I should have read it as an angsty teen, but it doesn’t deserve the press it gets.

    I like the rest of the list; perhaps a trip to the Tattered Cover this afternoon is in order.

  • Matt

    I am glad to see some people expressing distaste with Zen and the Art. It is the ramblings of an extremely intelligent individual, and food for thought, but if these books are meant to be read whilst on the road, I would say it is far too intellectual for my tastes. I prefer lighter fare while traveling; Travels with Charley is perfect. It has simple prose, inspiring diction, basic plot, straightforward events, and a dog. That’s all I need when I stumble into the tent at the end of the day.

  • Ryan

    #4 inspired and entire road trip of my own. I took my leave of my first “big boy” job after 5 years sold almost all my stuff, piled into a 15 year-old VW camper bus and traveled the country in a big donut shaped path from from Oregon to the Carolina’s up to Maine and back via the top of the country over about 6 months. At the ripe old age of 27 I decided I didn’t want to wait until I was 65 to see the Grand Canyon, Bryce, Zion, Outer Banks, Acadia, Glacier, Bad Lands etc and Blue Highways was my blueprint for traveling.

  • Mark

    Just finished Travels with Charley last week, and I’ve got Blue Highways on my Kindle ready to go when I finish A River Runs Through It.
    Another favorite not on the list: The Oregon Trail by Francis Parkman, recounting the author’s real-life trip across the West in 1846. I drove from Michigan to Montana last year, and it was amazing seeing how accurate his descriptions of the landscape still are. Plus, it’s old enough to be out of copyright, so it’s free for Kindle and on iBooks.

  • Robert Bass

    Good list. Steinbeck piece is one of my favorites and Bryson is a very clever weaver of words. But, what about one of the greatest road trips ever (though they had to pave their own path) . . . the journey of Lewis & Clark as outlined in Ambrose’s “Undaunted Courage.” A great read.

  • steven threndyle

    What’s a road trip list without books by some Brits, like Ted Simon’s Jupiter’s Travels and Dervla Murphy’s Full Tilt, and Redmond O’Hanlon’s In Trouble Again. One of the best subtitles I’ve ever seen is John Krich’s ‘Music In Every Room – Around the World in a Bad Mood.” Sort of tells you where he’s coming from. I’m off to SF next week, might have to hit the library and revisit Jack and Neil’s travels, and of course the time they meet up with Dean.

  • Anthony

    Bryson’s book on Australia is better in my opinion for true road trip – as he travels all of Australia, the good – bad – flat – boring – and fun.

  • Dean King

    Assuming the #10 spot is held for “fill in the blank,” off the top of my head, I vote for Charles Portis’s Dog of the South. It would be easy to do a list of the 99 best. . . . .

  • Riki

    Sidhartha is another one that’s prime roadtrip reading material.

  • Jay Jurkowitsch

    MORE by Kerouac : The Dharma Bums… it is road tripping up/down the West Coast and Up/Down the Sierra’s and Cascades!!

  • CR

    For me, just about any Cormac McCarthy novel will do the trick. Some of his books can be dark and violent as all hell, but the picture he paints of the desert southwest (or just about any landscape or setting) is amazing. On my last long trip I started with The Crossing, went back and read the rest of the trilogy, and then moved on to Blood Meridian. After that, I had to pick up Travels With Charley just to calm myself down a little.

    • steve casimiro

      I started my McCarthy journey with Blood Meridian. Talk about a headspinning way to enter an oeuvre.

  • Paul

    CR, I don’t know how you did it, man. Props though. And Steve, Blood Meridian is a tough place to start, but I think a good one nonetheless. I think the Orchard Keeper is probably his rawest and freest in terms of style, but as far as subject matter and readability goes, Blood Meridian takes the cake in raw. If you find yourself discouraged halfway through, don’t feel bad. Still, press on. You won’t regret it. I think you’ll find yourself compulsively grabbing his books despite a voice in heard head that tells you not to.

  • Davo

    If I’m camping, my favorite bring-along paperback is Bill Bryson’s /A Walk in the Woods: Rediscovering America on the Appalachian Trail/. Reviews that call a book “laugh-out-loud” are so clichied … but, yes, it always makes me laugh out loud at some point. It’s a veritable encyclopedia of what not to do when you’re camping, or trying to walk 2,200 miles.

  • dk

    Road Fever, by Tim Cahill. Well written and maybe the funniest thing I have ever read in my life.

  • Pat

    Over the decades, I’ve travelled a lot of the USA and Canada. I found The Nine Nations of North America (by Joel Garreau) aligned with my sense of place and culture over large areas. Really enjoyed Blue Highways. During travels, I’ve picked up regional accents. In backcountry huts, some groups I hang with have a ‘literary night’, for discussing recent reads. I’ve read aloud sections of Blue Highways, complete with my version of ‘merican accents.
    Thanks for the suggestions…

  • Pat

    Over the decades, I’ve travelled a lot of the USA and Canada. I found The Nine Nations of North America (by Joel Garreau) aligned with my sense of place and culture over large areas.
    For me at 30, with a major life change underway, I loved Sidhartha – thanks for the reminder to re-read it at age 67.
    Really enjoyed Blue Highways. During travels, I’ve picked up regional accents. In backcountry huts, some groups I hang with have a ‘literary night’, for discussing recent reads. I’ve read aloud sections of Blue Highways, complete with my version of ‘merican accents.
    Thanks all, for the suggestions…

  • Jared Hoke

    Blue Highways is a particular fave of mine, and for anyone interested, I EARNESTLY recommend you obtain the audio version read by the author. He has Mark Twain’s ear for the sound of American language, reads it wonderfully, and you can listen to him while ON the road. It doesn’t get any better than that.

  • Andrew T. Locke

    My favorite road trip book is one that was inspired by “On the Road,” “Zen & the Art of Motorcycle Maintenance,” & “The Electric Kool-Aid Acid Test.” It is an eBook titled “Looking Within: A Man’s Journey to Find Himself,” & it is available at this website: The first 20% of it can be downloaded for free, too. Looking Within’s blog:

  • Nathan

    Anything by Tim Cahill.

  • Richard

    “Out West” by Dayton Duncan should be on this list. It has helped inform my travels for over 25 years now. A little bit of Lewis & Clark and his own travels as well which is what brought him to the attention of Ken Burns.

  • Wade Nelson

    Zen and …. was the inspiration for a Florida to San Francisco off-Interstate trip with my buddy in his newly acquired ’64 Corvette. The book reads in thirds, a third about quality and Pirsig’s “Church of Reason”, a third about the trip itself, and a third the unreadable ramblings of a madman. The expository on quality alone is worth the read. Few Americans today could adjust a carburetor on a misfiring motorcycle. That intimate knowledge of how to repair one’s own vehicle, even basic repairs, is something lost in the day when you just go get a new Iphone to replace a broken one. Looking back, it the breakdowns, and the people who got us going again made the trip more meaningful than just a few memorable diners and campgrounds along scenic roads. I couldn’t read OTR, I yawned my way thru Blue Highways; for me ZAMM will always be the ultimate road trip book.

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