William Least Heat-Moon

Blue Highways: A Journey Into America by William Least Heat-Moon (1982)
Thanks to America’s sprawling interstate highway system, it’s all too easy to cross this country by car without actually seeing any of it. (And no, Wal-Marts and Waffle Houses don’t count.) In 1978, travel writer William Least Heat-Moon set out on a trip in which he made it his business to steer clear of billboard-choked mega-highways. Blue Highways recounts his meandering journey along America’s back roads, taking his beat-up van to towns like Nameless, Tennessee, and Liberty Bond, Washington. Along the way, he meets all sorts of uncannily wise folksy types, delves into issues of history and race, and searches for the perfect roadside café. (Hint: It has to do with how many old calendars a diner has up on the wall.)
Key vehicle: “Ghost Dancing,” a white 1975 Ford Econoline van
Quote: “A man who couldn’t make things go right could at least go. He could quit trying to get out of the way of life. Chuck routine. Live the real jeopardy of circumstance. It was a question of dignity.”


Jack Kerouac

On the Road by Jack Kerouac (1957)
Kerouac wrote the first draft of his frantic novel in three weeks on a 120-foot-long scroll, pausing only to glug down coffee and pea soup. He later added in fancy trappings like paragraph breaks, but the breakneck pace remained intact. On the Road became the seminal document of the Beat generation, tracing three years of quasi-spiritual cross-country road trips taken by Kerouac and his charismatic, womanizing buddy, Neal Cassady. (In the book, they go by the pseudonyms Sal Paradise and Dean Moriarty.) Following the pair as they ping-pong from New York City to San Francisco to Mexico City—and all the places in between—On the Road is an ode not only to a vanished, jazz-addled midcentury America, but also to the exuberant, borderline-stupid vigor of youth on the move.
Key vehicle: Moriarty’s (and Cassady’s) 1949 Hudson Commodore
Quote: “What is that feeling when you’re driving away from people and they recede on the plain till you see their specks dispersing?—it’s the too-huge world vaulting us, and it’s good-by. But we lean forward to the next crazy venture beneath the skies.”


John Steinbeck

Travels with Charley: In Search of America by John Steinbeck (1962)
Steinbeck first did the interstate journey narrative in 1939 with The Grapes of Wrath. But seeing as Tom Joad’s is probably the most depressing road trip ever committed to paper, your wanderlust would be better served by Travels with Charley, the author’s contemplative account of his meanderings across America with his wife’s French poodle. When Steinbeck was 58 and on the edge of retirement, he strapped a trailer to the bed of a pickup and hit the road, tracing a lazy circle around the country and shooting the breeze with everyone he meets. It would be the author’s swan song (he died four years after its publication) and according to his family, had more fiction in it than reality. But Travels nonetheless contains some of the truest observations about America and its people ever put to paper. Steinbeck was the master, after all.
Key vehicle: “Rocinante,” a forest-green 1960 GMC pickup truck equipped with a custom-built camper
Quote: “I saw in their eyes something I was to see over and over in every part of the nation—a burning desire to go, to move, to get under way, anyplace, away from any Here. They spoke quietly of how they wanted to go someday, to move about, free and unanchored, not toward something but away from something. I saw this look and heard this yearning everywhere in every state I visited. Nearly every American hungers to move.”


Hunter S. Thompson

Fear and Loathing in Las Vegas: A Savage Journey to the Heart of the American Dream by Hunter S. Thompson (1971)
Drugs! So many drugs. Hunter S. Thompson’s seminal piece of gonzo journalism is the kind of book that seizes you around the throat and throttles you just for the hell of it. The semi-true tale recounts the adventures of Raoul Duke (Thompson) and his “attorney,” Doctor Gonzo (Oscar Zeta Acosta), on a substance-addled road trip from L.A. to Vegas to cover the Mint 400 off-road race for Rolling Stone. In between bad trips on everything from acid to ether, Duke is hounded by put-upon traffic cops, angry editors, imaginary bats, and the creeping death rattle of 1960s counterculture.
Key vehicle: “The Great Red Shark,” Duke’s tricked-out red Chevy convertible
Quote: “Every now and then when your life gets complicated and the weasels start closing in, the only real cure is to load up on heinous chemicals and then drive like a bastard from Hollywood to Las Vegas. To relax, as it were, in the womb of the desert sun. Just roll the roof back and screw it on, grease the face with white tanning butter and move out with the music at top volume, and at least a pint of ether.”


Robert M. Pirsig

Zen and the Art of Motorcycle Maintenance: An Inquiry Into Values by Robert M. Pirsig (1974)
A cult phenomenon when it was first published (after much rejection) in the 1970s, this meandering novel is equal parts road-trip narrative and philosophical treatise. Mixing truth and conjecture, Pirsig recounts a motorcycle trip from Minnesota to California with his 12-year-old son and two friends. It’s also the story of “Phaedrus,” the person that the narrator was before he was subjected to creepily heavy doses of electroshock therapy—a guy obsessed with combining Eastern and Western philosophical ideas into a grand whole that he calls “Quality.” Whether he’s describing Euclidean concepts or the feel of riding a hog through rural Montana, Pirsig is as earnest as he is erudite. Pretty much the only thing this novel won’t teach you about, ironically enough, is how to fix a motorcycle.
Key vehicle: Pirsig’s 1964 CB77 Honda Super Hawk
Quote: “So we move down the empty road. I don’t want to own these prairies, or photograph them, or even stop or even keep going. We are just moving down the empty road.”


Chuck Klosterman

Killing Yourself to Live: 85% of a True Story by Chuck Klosterman (2005)
On an assignment for Spin, navel-gazing essayist Chuck Klosterman embarked on a whirlwind 6,557-mile pilgrimage around the country. His holy sites: the locations of famous rock ’n’ roll deaths, from the Chelsea Hotel (he unfortunately didn’t get to the inside of Sid and Nancy’s room) to the Seattle backyard where Kurt Cobain shot himself. As in much of his writing, Klosterman views America through the bifocals of music and infatuation, reflecting on the women he’s slept with and waxing philosophical about the Replacements and Fleetwood Mac (and smoking quite a lot of weed). The author’s trademark deadpan humor pervades the book, whether he’s lost in rural Mississippi or shooting the breeze at a North Dakota motel bar. Don’t expect profound insights on senseless death, but do expect to slowly construct the perfect playlist for your own American odyssey.
Vehicle: “The Tauntaun,” Klosterman’s rental silver Ford Taurus
Quote: “I am one of the worst drivers in America. I don’t miss driving at all, and I’m probably the worst candidate imaginable for a cross-country road trip. However, I do miss Car Rock, and I miss it profoundly. I love the way the music inside a car makes you feel invisible; if you play the stereo at maximum volume, it’s almost like other people can’t see into your vehicle. It tints your windows, somehow.”


Neil Gaiman

American Gods by Neil Gaiman (2001)
What’s better than an all-American road trip? An all-American road trip with freakin’ Odin. Like the deities, demigods and djinns in his novel, British fantasy author Neil Gaiman came to the U.S. from the Old World. American Gods is his roundabout way of talking about the weirdness of the expat experience, as he sends the King of Asgard and his bodyguard on a transcontinental odyssey to find the mythical figures—Anubis, Czernobog, Johnny Appleseed—living among us. En route, they visit weird American landmarks like Wisconsin’s House on the Rock and the geographic center of the U.S. in Lebanon, Kansas. Shadow, the novel’s cipher of a protagonist, is almost beside the point; American Gods is about what old concepts like belief and home mean in a country that is constantly reinventing itself.
Key vehicle: Shadow’s white 1983 Chevy Nova, generally referred to as “the piece of shit”
Quote: “‘This is the only country in the world,’ said Wednesday, into the stillness, ‘that worries about what it is.… The rest of them know what they are. No one ever needs to go searching for the heart of Norway. Or looks for the soul of Mozambique. They know what they are.’”


Simone De Beauvoir

America Day by Day by Simone de Beauvoir (1954)
There are precious few American travelogues out there written by women. But you couldn’t ask for a more interesting observer than French philosopher-feminist Simone de Beauvoir, who chronicled her four-month wander from New York to the West Coast to the Deep South in this journal-style account. She’s overwhelmed by Manhattan, hangs out in Chicago with her lover, novelist Nelson Algren, before tooling around California and traveling by bus from Nevada to Florida. Along the way, she tackles issues like identity and race, and searches out the best live jazz America has to offer. So basically, Kerouac sans the beatnik machismo. L’Amérique au jour le jour wasn’t published in English until the late ’90s—better late than never, we guess.
Vehicle: A series of trains, buses and rides from friends.
Quote: “I think that America is a world, and that you can no more accept or reject a world than you can accept or reject the world. It’s a matter of choosing your friends and enemies, of asserting your projects and your singular revolts. America—a piece of the planet, a political system, a civilization; classes, races, sects, and men taken one by one.”


John Waters Carsick

Carsick: John Waters Hitchhikes Across America by John Waters (2014)
At the age of 66, the legendary shock-camp filmmaker decided to do something pretty crazy, even by his standards: travel the 2,800-odd miles between his beloved Baltimore and his crash pad San Francisco entirely via hitchhiking. He flagged down cars with a scrawled-on cardboard sign instructing drivers to take him to the end of Interstate 70 West. Some drivers recognized his iconic pencil mustache; others thought he was a particularly odd hobo; all of them were at least a little bit entertained. In true Waters fashion, a good chunk of Carsick is dedicated to invented scenarios of what might befall him on the trip (drag queens, vice squads, sexual favors). What actually happens isn’t nearly so harrowing, but it’s still delightful. Who wouldn’t want to run into the man responsible for Pink Flamingos at a Junction City Holiday Inn?
Vehicle: Anything anyone lets Waters climb into.
Quote: “I’m alive, I think, and so many of my friends are not. I may be nuts to be doing this, but I’m kind of proud of myself. I am having an adventure. I like my life. Even if I have to stand here for the rest of it.”


Tom Wolfe 1972

The Electric Kool-Aid Acid Test by Tom Wolfe (1968)
In some drug-addled nowhere-space between On the Road and Fear and Loathing lies The Electric Kool-Aid Acid Test, Tom Wolfe’s account of his time spent among Ken Kesey and his Merry Pranksters. The imagery is iconic by now, almost a parody of itself: a psychedelic bus packed full of hippies tripping on LSD, Kesey as cult leader, no less than Neal “Dean Moriarty” Cassady at the wheel. But at the time of its publication, the book was groundbreaking; its bombastic, stuttering subjective prose helped to usher in the age of New Journalism. And it’s still one of the wilder road-trip narratives out there; whether the big rainbow bus is careening along the Blue Ridge Highway or the Pranksters are rubbing elbows with the Hells Angels, Acid Test is a trip in more ways than one.
Vehicle: “Furthur,” a tricked-out school bus painted all the colors of the rainbow
Quote: “‘There are going to be times,’ says Kesey, ‘when we can’t wait for somebody. Now, you’re either on the bus or off the bus. If you’re on the bus, and you get left behind, then you’ll find it again. If you’re off the bus in the first place—then it won’t make a damn.’ And nobody had to have it spelled out for them.”