5 Best Road Trip Classics of All Time

Here’s our round-up of enduring road trip classics that will help you keep that summertime adventurous feeling going strong all year long.

Road trip reading

With summer winding down into its dog days and road-trip season coming to an end, many of us long to recapture the magic of the road. Thankfully, the annals of literature are chock-full of classics that aim to do just that, allowing us the sense of freedom that summer sun and flying down the highway evoke. Here’s our round-up of enduring road trip classics that will help you keep that summertime adventurous feeling going strong all year long.

1. On the Road, by Jack Kerouac

“Whither goest thou, America, in thy shiny car in the night?”

We know, it’s a gimme. But it’s hard to beat (get it?) this all-time American classic. In an age when the world hadn’t yet heard of fossil fuels and the ozone layer, and the road still represented boundless freedom and possibility, Kerouac’s classic inspired generations to seek excitement (and themselves) behind the wheel.

Legend holds that Jack typed his opus in 3 Benzedrine-fueled weeks at about 100 words per minute on a scroll composed of letter-sized sheets taped together at their ends. And while the truth is that Jack wrote, revised, and rewrote the novel over the course of 6 years while trying to find a publisher, the scroll part is true.

You can pick up a faithful reproduction of the original draft in trade paperback form, or find an unabridged edition of the audio version read by another American literary legend, Cormac McCarthy.

2. Travels With Charley: In Search of America, by John Steinbeck

“We find after years of struggle that we do not take a trip; a trip takes us. …The certain way to be wrong is to think you control it.”

In this ostensibly true travelogue, Steinbeck sets out from his Sag Harbor, Long Island, home with his full-size poodle, Charley, to take a turn around the whole of the United States. Behind the wheel of his pickup truck, Rocinante (a nod to another quixotic traveler and literary giant), Steinbeck visits and details Deer Island, Maine; Niagara Falls, New York; Yellowstone Park; California’s Avenue of the Giants (where he comes closer than any author to capturing the breathtaking stateliness of giant redwoods); his beloved Monterey; and dozens of other notable sites.

If you’d like to model your drive off Steinbeck’s, check out this interactive map. An audio version read by actor Gary Sinise is available.

3. The Electric Kool-Aid Acid Test, by Tom Wolfe

“You’re either on the bus or off the bus.”

Tom Wolfe, one of the founders of the “New Journalism” movement, which sought to bring voice and creativity back to the supposedly objective world of news journalism, got on the bus (Furthur) with Ken Kesey (author of One Flew Over the Cuckoo’s Nest) and a cohort of hippies (the Merry Pranksters) to “prank” the United States. “Prank” here translates to “attempt to open people’s minds through the liberal application of hallucinogens.” While we certainly wouldn’t suggest replicating any of Neal Cassady’s driving techniques (who was, not at all coincidentally, also the primary driver in On the Road), the book makes for some raucously fun road reading — not to mention an invaluable portrait of hippie America.

You’ll find cheap paperback copies of this one in just about any used bookstore on the planet, and audio versions should be equally easy to track down.

4. James and the Giant Peach, by Roald Dahl

“Both of them suddenly got eaten up (in full daylight, mind you, and on a crowded street) by an enormous angry rhinoceros which had escaped from the London Zoo.”

While not really a road trip book, it’s an all-time favorite, and revolves around a rather fantastic journey, making it a good choice for those looking to recapture a slice of their childhood or just a good bedtime story for the kids. Packed with magic seeds, insects “as large as a large dog,” and a humungous, flying stone fruit, Dahl’s classic proves entertaining for kids and just delightfully twisted enough to engage adult minds too.

You can pick up an audio version of the book that includes Charlie and the Chocolate Factory, Fantastic Mr. Fox, and The Enormous Crocodile too — best of all, the author does the reading himself.

5. I’m a Stranger Here Myself: Notes on Returning to America After 20 Years Away, by Bill Bryson

“Of all the things I am not very good at, living in the real world is perhaps the most outstanding.”

After living in England for 2 decades, American author Bill Bryson returns to the states and starts a cross-country road trip, making hilarious and insightful observations along the way. He travels (alone) through the Heartland, the Deep South, the tiny Northeastern states, and the sprawling West, trying to rediscover (and make sense of) his native country. Short of loading a sleeping bag in the car and driving a few thousand miles across the states and back, this book is the best way to experience all the beauty, quirk, contradiction, and vastness that is America.

Audio and good-ole-fashioned print versions of the book are available in all the usual places.

Have a road-trip-related favorite we missed? Tell us all about it on our Facebook page.

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