10. 'Cross Country'
By: Robert Sullivan
Cross Country is Robert Sullivan's travel memoir of a family trip from Portland to New York City. Over the course of the 2,900 miles, Sullivan's mood alternates between eagerly recounting historical aspects of Lewis and Clark's expedition and exasperatedly dealing with 40-plus hours of driving in a car of less than enthusiastic kids. Isn't it these grueling moments that ultimately bring families together?
9. 'A Walk Across America'
By: Peter Jenkins
Peter Jenkins is now a celebrated travel writer in his mid-60s, but his first book, A Walk Across America, recounts a journey he took during his 20s. Walking from his college town in New York all the way to New Orleans, Jenkins meets people of varying backgrounds and demographics, discovering America at the same time he discovers more about himself.
8. 'Rolling Nowhere'
By: Ted Conover
Rolling Nowhere isn't so much a road trip as a "rail trip." Beginning in St. Loius, Conover's interest isn't the Wild West; his focus is on the hobo culture, including how they get around the country and how they transfer their knowledge throughout the community. If anthropological studies are more in line with your cup of tea, this might be the journey for you.
7. 'Blue Highways'
By: William Least Heat-Moon
William Least Heat-Moon's book is named for the backwoods roads that connect America's smaller cities, labeled as blue on old road maps. Published in 1982, Heat-Moon's desire to seek out locally-owned establishments while he circled the country seems right at home with the locavore happening today.
6. 'The Lost Continent'
By: Bill Bryson
Bryson set out from his hometown of Des Moines, Iowa, shortly after his father died. The humor he found in his experiences traversing the Eastern United States helps him to cope with and make sense of the memories he has of his father. This is one of those trips that reveals more about the person who takes it than the people encountered along the way.
5. 'The Electric Kool-Aid Acid Test'
By: Tom Wolfe
Wolf is along for the ride with Ken Kesey and his "Merry Pranksters" who travel across the whole country. The title refers to the LSD parties the group promoted trying to achieve altered states of mind while leaving behind the worries of the world. The book brought hippie culture to the mainstream and served as inspiration for many others to go on similar journeys themselves.
4. 'Travels with Charley'
By: John Steinbeck
Just six years before his death, Steinbeck set out to see the country one last time, along with his poodle Charley. While many argue that much of this travel literature is fiction (you do know he is a novelist, yes?), the sentiments and overall feelings about the journey that Steinbeck comes to are most certainly authentic.
3. 'Fear and Loathing in Las Vegas'
By: Hunter S. Thompson
The shortest of the road trips on this list, Thompson travels from L.A. to Vegas and back. Championed today as the bible of counterculturalism, Fear and Loathing is a psychedelic surreal romp that only borders on the coherent. Is the point to figure out what's real and what's imagined? No. Just sit back, live in the moment, and enjoy the ride.
2. 'Zen and the Art of Motorcycle Maintenance'
By: Robert M. Pirsig
This philosophical exploration into the meaning of life, the pursuit of understanding, and the ways in which to perceive the world is hidden underneath a father and son's journey from Minnesota to California. Don't be scared away by the dense nature of the book's themes, however. The only intimidating thing about this story is 1,700 miles they drove without a windshield.
1. 'On the Road'
By: Jack Kerouac
On the Road is the granddaddy of all literary road trips. While this is a work of fiction, it has its basis in Kerouac's actual journeys from 1947 to 1950. The sexual content and drug use initially shocked at the time of its printing, but the book has since become an integral part of American literature and influenced other works like it, Fear and Loathing among them.