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On the Road: 5 Classic American Road Trips Taken by 5 Famous Writers

Nancy Bilyeau
US Highway 163. The road leading to Monument Valley, Utah.
US Highway 163. The road leading to Monument Valley, Utah.

Some great literary figures of the past have embarked on some classic road trips throughout the USA. The image of the open road has something quintessentially American about it. Perhaps nowhere else in the world is the road trip as romanticized as it is in the States. And rightly so. There is a long lineage of famous road trips undertaken by giants of literature which have become embedded deep into the culture and landscape. And for many, literary road trips re-creating the classic journeys of famous writers, holds great appeal. even offers routes to some of the most famous (some may say infamous) road trips across North America, inspired by well-known works of literature.

“A  journey by car is a different kind of travel, providing a freeing feeling where you can call all of the shots,” said CarRentals. “Many authors who have written classic literary novels aren’t all that different, with stories exploring national parks, new cities, and cultural events.”

Jack Kerouac road trip
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One of the most famous road trips of the last century was depicted in Jack Kerouac’s On the Road. In 1954 Kerouac had a vision in a Massachusetts church that told him the real meaning of “Beat” was “Beatific,” converting alienation into spiritual transcendence. On the Road, first published in 1957, introduced “the Beat generation.” In this novel of life on the road, Dean Moriarty and Sal Paradise, Kerouac’s fictional alter ego, search for ecstasy, taking them from New York City to San Francisco and in one final trip down into Mexico, getting their kicks from all-night talk sessions, drunken parties, orgies, and an exploration of jazz. Behind the wheels of numerous automobiles, the two young men zigzag across the continent “leaving confusion and nonsense behind and performing [their] one and noble function of the time, move.”

F. Scott Fitzgerald road trip
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A far earlier road trip was that of F. Scott Fitzgerald and his wife, Zelda, in 1920. Seeking the feeling of hope and freedom of the open road, the Jazz Age couple set out on a 1,500-mile road trip from Connecticut to Alabama, Zelda’s native state, in an automobile they dubbed the “Rolling Junk.” It was a 1200-mile quest for the biscuits and peaches Zelda missed in her home in the north. In a 1934 letter to his editor Max Perkins, Fitzgerald described it as “a long, supposedly humorous account of an automobile journey.”

Robert Pirsig road trip
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Zen and the Art of Motorcycle Maintenance, published in 1974, takes a different tone. It is the story of a man and his son who go on a motorcycle trip from Minnesota to California, choosing the back roads and sleeping overnight in motels or camping. “On another level, it’s a dense philosophical look into the conflict between romantic and classical thinking,” wrote one admirer. “Along the way the author explains his search for and belief in quality as a unifying force. He uses the trip and the characters in the book as metaphors to discuss philosophy.”

Ken Kesey road trip
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Tom Wolfe’s book The Electric Kool-Aid Acid Test is often celebrated as the starting point of the psychedelic 1960s. The story follows Ken Kesey and his band of followers, the Merry Pranksters, as they drive a painted bus across the country under the influence of drugs, eclectic music and multimedia experiences to transcend reality and bring a higher state of consciousness during the height of the counterculture. Their trip travels across the country from California to New York, north to Canada and back again.

Hunter S. Thompson road trip
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But perhaps the wildest road trip of all was that of Hunter S. Thompson. His book Fear and Loathing in Las Vegas drew from two magazine assignments, one from Rolling Stone and the other from Sports Illustrated. The story follows its protagonist, Raoul Duke, and his attorney, Dr. Gonzo, from Los Angeles to Las Vegas. This cult classic of gonzo journalism is the best chronicle of drug-soaked, addle-brained good times ever written. It is also the tale of a long weekend road trip that has gone down in the annals of American pop culture as one of the strangest journeys ever undertaken.

Related Article: Psychedelic Celebrity Cars of the 1960s

The Great American Literary Road Trip is a wonderful part of the history and heritage of the USA. If you’d like to learn more about these classic road trips and discover more routes please visit the CarRentals blog as well as their site: