This list was compiled by BRENDAN LEONARD – and I am so excited to start chipping away at this list and hopefully agree with him!
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.
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.