Recreating Three of American Literature’s Most Iconic Road Trips

The American landscape has long inspired travelers, trailblazers, and adventurers — from the covered-wagon pioneers of the Westward Expansion, to wanna-be hippies hitchhiking to San Francisco in search of free love, happiness and hallucinogens, to station wagons full of families headed for the Grand Canyon. And even though it’s now possible, thanks to technology, to virtually visit nearly any location in the world, there is still something irresistible about a good old-fashioned road trip

Are you itching to travel the nation’s highways and byways? If you just can’t wait to get on the road again, why not give your trip a little structure and a whole lot of fun by recreating one of the iconic road trips from American fiction?

First Things First: Deciding How to Travel

Jack Kerouac and his companions traveled via Greyhound bus when they weren’t taking their chances by thumbing rides. The father and son pilgrims in Zen and the Art of Motorcycle Maintenance make their way by — spoiler alert! — motorcycle.  And a psychedelic-hued school bus is the method of conveyance for the heroes of The Electric Kool-Aid Acid Test.

While recreating these modes of transportation is technically possible, it’s probably a better idea to travel by recreational vehicle. It will help you save big on accommodations, carry along the comforts of home, and see all the roadside attractions that are to be seen. Make sure to tuck away some extra cash for emergency repairs, and look into Good Sam motorhome warranties, which are another smart safeguard.

On the Road

The magnum opus of the beatnik canon, Jack Kerouac’s On the Road inspired a generation of cool cats to reject traditional values while searching for meaningful relationships and experiences. The book is part picaresque novel, part barely disguised memoir, and 100% the gold standard for the road-trip trope that has become a literary classic.

Kerouac’s fictional counterpart, Sal Paradise, starts his journey in New Jersey, makes a brief pit stop at NYC’s White Horse Tavern, then sets off across the country — destination San Francisco. Along the way he makes memorable visits to Chicago and Denver.

There are plenty of Kerouac-related stops that are worth making, particularly for diehard fans, but every road tripper who ends up in Frisco should head for Jack Kerouac Alley for a photo op. After that, be sure to stop in at Vesuvio, one of the famous beatnik’s favorite bars.

Zen and the Art of Motorcycle Maintenance

Described as a “fictionalized autobiography,” Ken Pirsig’s modern classic Zen and the Art of Motorcycle Maintenance tells the tale of his journey from Minnesota to Northern California. He and his son, along with two traveling companions, engage in deep philosophical conversations along the way — so this is a great road trip to make if you are in search of the ever-elusive meaning of life. 

The route meanders through the Dakotas, Montana, Idaho, and Oregon before heading south along the coast of California — which means that anyone following in Pirsig’s footsteps (or, more accurately, tire treads) will be treated to some of the most stunning landscapes in the country. This is Big Sky Country, after all. 

For Pirsig, an integral part of the experience was eliminating the barriers between self and environment that a car necessarily imposes. “On a cycle the frame is gone,” he writes in Zen. “You’re completely in contact with it all. You’re in the scene, not just watching it anymore, and the sense of presence is overwhelming.” 

However, that doesn’t mean you can’t still appreciate the scenery and splendor of these northern states. You’ll just have to stop to smell the roses a little more often. 

The Electric Kool-Aid Acid Test

What do you picture when you think about 1960s America? If it’s colorfully dressed hippies tripping on psychedelic drugs and “tuning out” by eschewing social mores, then you have Tom Wolfe’s epic creation, The Electric Kool-Aid Acid Test, to thank. In it he chronicles the adventures of Ken Kesey — an enormously influential counterculture figure who is generally considered the essential link between the beatniks and the hippies — and his followers, called the Merry Pranksters.

Kesey and the Pranksters begin their literal journey in La Honda, California, and their travels roughly coincide with the perimeters of the U.S., with sojourns to both Canada and Mexico. Traveling every mile that their converted school bus explored would require a fairly significant investment of both time and money, so you may want to limit your Acid Test road trip to just one of the original legs. 

Naturally, we can’t condone emulating the Merry Prankster’s heavy use of hallucinogenic drugs, either — but there are plenty of attractions and points of interest along the way to keep your mind occupied without being altered.

Inspired to Hit the Road?

These days, taking a cross-country drive to immerse yourself in American culture is a little less of an adventure — can you imagine Kerouac looking up the best local hamburger joints by logging onto Yelp? — but there are certainly some advantages to being connected while exploring parts unknown. For starters, it’s easier than ever to plan out your pit stops so that you maximize each and every hour of your epic road trip. And there’s nothing quite like Instagram for showing off your vacation pictures!

Have you ever driven across the country? Any can’t-miss attractions, sights, or restaurants you care to share with your fellow travelers? Let us know in the comments!


Tom Brown
Tom Brown is an automotive market enthusiast living in the United States. He holds a diverse background in automotive marketing and enjoys utilizing that to produce insights into the inner workings of the industry.