The Ultimate List of Epic Road Trip Books

The Ultimate List of Epic Road Trip Books

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A great book has the power to not just take you along for the ride with the author but to instill in you the burning desire to hit the road yourself. This list of Epic Road Trip Books is sure to keep you busy for a while and will make you want to hand your boss your two-weeks notice and start packing your bags.

I put this list together as I get ready to launch my own road trip book, The Road Always Leads West.

This is part IV in my series of posts on Road Trip Planning and Inspiration.

Get inspired for your next road trip with this Ultimate List of Epic Road Trip Books

5 Must Read Road Trip Reads

On the Road by Jack Kerouac

(1957)

We might as well get this one out of the way first, it’s easily the most well-known road trip book ever written, a book which has inspired generations and countless imitations.

Kerouac’s classic book On the Road that details his travels with his friends as they travel across America. The book was heavily steeped in the jazz and poetry culture and is considered the defining work of the Beat Generation, which so influenced the counter culture movement of the 60s.

The book is available as it was first published or you can get the Original Scroll version which was released as written by Jack Kerouac on a continuous sheet of paper 120’ long and which features the real names of his friends, not pseudonyms.

The Ultimate List of Epic Road Trip Books

Blue Highways by William Least Heat-Moon

(1982)

Heat-Moon set out to put the past behind him by setting out on the open road. The premise of the book is his travels along the smaller roads, marked blue on the map, and discover small town America.

His travels to small town America show a country on the verge of change with the increasing homogenization through fast food culture and strip malls.

Heat-Moon does a great job featuring the lives of the people he meets along the way, a curious cast of characters who live in “those little towns that get on the map—if they get on at all—only because some cartographer has a blank space to fill.”

The Ultimate List of Epic Road Trip Books

Travels with Charley in Search of America by John Steinbeck

(1962)

In September of 1960 John Steinbeck, already a successful author, set out to rediscover an America that he worried he had lost touch with. According to Steinbeck’s son, the real reason for his journey was that he knew he was dying and he wanted to see the country one last time.

Steinbeck set out on a giant cross country journey from New York, up to Maine, across to the west coast, down to California then across the southern half of the states back east, before venturing back up the East Coast. Essentially completing a massive circular journey through America.

He had his French poodle Charley in tow throughout his journey through a “New America” that was on the cusp of some great upheaval.

Steinbeck was 58 when he set out on this journey alone (well, with a dog), which just goes to show that isn’t just for young, aimless, 20-somethings.

The Ultimate List of Epic Road Trip Books

Zen and the Art of Motorcycle Maintenance by Robert Pirsig

(1974)

Part philosophical treatise and part motorcycle road trip across the northern stretch of the United States and then down to California.

Zen and the Art of Motorcycle Maintenance tells the story of a father and son motorcycle trip with a pair of friends but also delves into fundamental questions about how to live life and tries to reconcile science, religion and more.

A powerful read that will not only inspire you to hit the road, but inspire you to examine your own perspectives on some of these central themes of life.

The Ultimate List of Epic Road Trip Books

The Kindness of Strangers: Penniless Across America by Mike McIntyre

(1996)

Not a traditional road trip book where the driver is behind the wheel on the open road, but rather Mike decided to hitchhike across the country from San Francisco to Cape Fear, North Carolina, which would be challenging in and of itself. But Mike decided to do it without so much as a penny.

He would have to rely on the goodwill and help of complete strangers on the open road in order to find rides, eat, and have a place to sleep.

It’s an incredible journey and an even more incredible story which highlights the stories and generosity of the folks that he meets along the way.

The Ultimate List of Epic Road Trip Books

Five books isn’t enough for you? Well, I’ve got another 10 awesome road trip books below and then a number of reader suggestions.

 

10 More Great Road Trip Reads

The New American Road Trip Mixtape by Brendan Leonard

(2013)

Brendan Leonard has become one of the leading modern voices for road trips and the transformative nature of nature and the great outdoors.

Post-breakup Brendan set out by himself to explore the American West as he lived in the back of his station wagon. This book tackles the American Dream and the call of the open road in Brendan’s humorous and unique style.

His most recent book, Sixty Meters to Anywhere, is an incredible read about overcoming alcoholism and finding himself through climbing.

The Ultimate List of Epic Road Trip Books

Into the Wild by Jon Krakauer

(1995)

Krakauer’s book is not strictly a road trip book, nor is it a first-person book about a road trip, but rather traces the incredible story of Chris McCandless and his nomadic wanderings.

After graduating college back east, Chris donated what remained of his college fund and drove west, eventually abandoning his car and hitchhiking across the west for a number of years. His travels led him to a Walden’s Pond type existence in the Alaskan bush where he was found dead.

The book has a sad end, but the story of his travels and Krakauer’s incredible writing will inspire you to hit the road in Chris’ footsteps undoubtedly. I know it did for me.

The Ultimate List of Epic Road Trip Books

The Lost Continent by Bill Bryson

(1989)

Bill Bryson is one of the best travel writers out there, able to turn the simplest or seemingly boring concepts into insightful, interesting, and often humorous reads.

After living abroad in the United Kingdom for many years, Bryson sets out to rediscover America by visiting it’s small towns.

Bryson’s book about hiking the Appalachian Trail, A Walk in the Woods, is still one of my favorites.

* Wish you could travel more and more affordably? Click here to grab my free course and resources that will show you exactly how I've been able to travel for more than four years.


The Ultimate List of Epic Road Trip Books

Drive Nacho Drive by Brad Van Orden

(2014)

Drive Nacho Drive tells the story of Brad and his wife Sheena quitting their jobs, giving up the American Dream and driving south in their old beat-up Volkswagon Van named Nacho.

The road takes them through all of Central America, past the Darien Gap to South America and finally to the “end of the earth” in Patagonia where the Pan-American Highway finally ends.

A pretty incredible read that might just inspire you to think about taking your road trip international (like Andrea and I recently did).

The Ultimate List of Epic Road Trip Books

The Cruise of the Rolling Junk by F. Scott Fitzgerald

(1924)

Another of America’s finest authors sets out on the open road, this time F. Scott Fitzgerald of Great Gatsby fame, who sets out with his wife Zelda on a drive from Connecticut to Alabama.

These serialized articles compiled into a book of their journey in a dilapidated car (the rolling junk) and tells the story of a younger America.

The Ultimate List of Epic Road Trip Books

Killing Yourself to Live by Chuck Klosterman

(2005)

Chuck Klosterman set out on a road trip exploring the deaths of famous musicians across America.

He covered nearly 7,000 miles as he visited the place where Buddy Holly’s plane crashed, where Kurt Cobain committed suicide, or Jeff Buckley drowned in a river.

An interesting basis for a road trip, for sure.

The Ultimate List of Epic Road Trip Books

Fear and Loathing in Las Vegas by Hunter S. Thompson

(1971)

A wild and drug fueled road trip to Las Vegas by the one and only Hunter S. Thompson.

The book, beyond the manic drug addled scenery, paints a different picture of Las Vegas, one that had not yet been taken over by the larger than life hotels and commercialization of the Strip.

The Ultimate List of Epic Road Trip Books

American Nomads by Richard Grant

(2003)

Richard Grant spent more than 15 years wandering the American West alongside the hobos, truckers, retirees, and hippies, documenting the lives of those who wander the American West.

Grant examines the myths and realities of the often romanticized open road, while also examining the sedentary nature of the American Dream.

He contrasts the stories of modern wanderers with the historical characters, the frontiersmen and conquistadors, who set loose upon this same landscape centuries ago.

The Ultimate List of Epic Road Trip Books

The Electric Kool-Aid Acid Test by Tom Wolfe

(1968)

Neal Cassady, who also is featured prominently in Kerouac’s On the Road, set out to drive Ken Kesey and the Merry Pranksters’ bus across America in a psychedelic LSD-fueled mission that takes road “trip” to a whole new level.

The book offers a look into the hippy, counter-culture movement of the 1960s.

The Ultimate List of Epic Road Trip Books

Jupiter’s Travels by Ted Simon

(1979)

Ted Simon spent an astonishing four years driving around the world on the back of a motorcycle in the late 70s. I actually had the chance to meet Ted at the Overland Expo.

He set out from London for more than 63,000 miles through 45 countries in Africa, South America, Australia, Asia, before arriving back home.

An incredible journey in the days before cell phones and internet, and all done solo with no support team or social media updates.

The Ultimate List of Epic Road Trip Books

7 More Reader Suggestions

I reached out to friends, followers, and readers of this blog for a few of their favorite road trip books. Here’s what they recommended.

Traveling Music by Neil Peart

The drummer for Rush explores the inextricable link between road trips and music, how music is the soundtrack to our lives, by telling autobiographical stories based on music from a solo road trip.

Road Scholar by Andrew Codrescu

The Romanian-born writer sets out in the shadows of Kerouac as he discovers America behind the wheel.

One for the Road by Tony Horowitz

Tony set off on a 7,000 mile adventure through the Australian Outback.

Roads: Driving America’s Great Highways by Larry McMurtry

Larry has written an homage to the road itself, where the route is the destination and not just a means.

Catfish and Mandala by Andrew X. Pham

A journey by bicycle through Mexico, Japan and on to Vietnam as Andrew (born in Vietnam but raised in California) travels he also confronts issues of cultural identity, immigration, and more.

Ghost Rider by Neil Peart

Another book by the drummer from Rush, this time Neil hits the road soon after losing his wife and daughter within a year of one another.

A Walk Across America by Peter Jenkins

More than 25 years ago Peter set out to walk from New York to New Orleans in the company of his trusty dog, not quite a traditional road trip, but definitely in the same spirit.

What would you add to this list? Sound off in the comments below.

The Road Always Leads West

Of course, I’d be remiss not to mention that you check out my book The Road Always Leads West if you love a good road trip story… 🙂  

https://www.youtube.com/watch?v=4iV3J-eDsPo

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Get inspired for your next road trip with this Ultimate List of Epic Road Trip Books

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The Ultimate List of Epic Road Trip Books

Ryan

Author, Writer, and Head Honcho at Desk to Dirtbag
Ryan is an author, adventurer, perpetual wanderer, and self-proclaimed dirtbag (but that might not mean what you think). Originally from Seattle, he headed to Washington D.C. where he spent five years working for Congress before heeding the call of the wild. He set out living in his pickup truck to road trip across the American West. Since then he backpacked through Colombia, drove across all of Central America, and also wrote a best selling book: Big Travel, Small Budget. He just finished driving his old truck across all of South America -- support the adventures by visiting the D2D Shop. Follow the adventures on social media or read more about me.

Comments 1

  1. Hey Ryan,

    Thanks for the list. I read a lot while travelling. It’s very meditative and relaxing for me. A few of these I have read, but I plan on adding to my list with a few of these books. I always use my kindle too, as it’s much lighter and holds thousands of books.

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