1. On The Road by Jack Kerouac
The quintessential slice of countercultural Americana.
What to pack: Drugs, some good jazz, and a heaping scoop of generational disillusionment.
2. Wild by Cheryl Strayed
Or "How To Get Your Shit Together And Not Die Doing It In 100 Days Or Less — A Last-Ditch Guidebook."
Pit stops: Death, depression, addiction, self-discovery, mangled toenails, triumph.
3. Fear And Loathing In Las Vegas by Hunter S. Thompson
Like On The Road, here's another raunchy roman à clef totally riddled with drugs and debauchery.
1) Show up to report on a motorcycle race
2) Do all the drugs instead
3) Like, all the drugs
4) Trip hard
5) Wreck stuff
6) Reflect on stuff
4. The Lost Continent by Bill Bryson
Bryson eschews tourist traps for a wry (and sometimes curmudgeonly) romp across small-town America, rediscovering his homeland after living across the pond for too long.*
What to pack: A sense of humor.
*For something less biting and a little more Appalachian, consider A Walk in the Woods.
5. Travels With Charley by John Steinbeck
A more even-handed appraisal of America's heartland, at once charming, provocative, and beautifully bittersweet.
What's that smell?: Charley the poodle. Also too many antique shops. And disheartening racism.
6. Reservation Blues by Sherman Alexie
This may very well be your only opportunity to follow an all-Native American R&B band on tour from Seattle to NYC. Alexie's blend of humor, magical realism, and heart is not to be missed.
I Spy: An enchanted guitar. That's basically all you need to know.
7. Assassination Vacation by Sarah Vowell
Or "Everything You Never Knew You Needed To Know About The First Three Assassinated Presidents." Also "How To Roadtrip From New Hampshire To Alaska Without A Driver's License."*
What to pack: A bulletproof vest. And your "History Geek" hat.
*This one's also great as an audiobook, seeing as Vowell is a contributing editor for "This American Life" and voiced Violet in Pixar's The Incredibles. And she ropes in a star-studded cast to lend their voices, including Stephen King, Catherine Keener, Conan O'Brien, and Jon Stewart. *fans self*
8. Blue Highways by William Least Heat-Moon
An engrossing, measured, and meandering portrait of America's back roads, as told through Heat-Moon's poignant interactions with the people he meets along the way.
Pit stops: Basically every city in the U.S. — or 562 of them — from Annaquatucket, RI, to Zwolle, LA.
9. Black Boy by Richard Wright
Wright's memoir of his childhood in the Jim Crow South charts a sobering path across poverty, pain, and perseverance. It is an unrelenting record of injustice and one man's journey to understanding his history and himself.
I Spy: So much trauma.
10. Into The Wild by Jon Krakauer
A meticulous and compelling recollection of Christopher McCandless's ill-fated solo journey into the Alaskan wilderness.
1) Graduate from college
2) Donate life's savings to charity
3) Abandon car and all material possessions
4) Burn remaining cash
5) Change name
6) Find work on the road
7) Enter Alaska
11. A Walk Across America by Peter Jenkins
A definitive "oldie but a goodie," Jenkins's 1973–75 walk from New York to New Orleans remains just as relevant and affecting forty years later — truly an impressive...feet. (Sorry.)
Itinerary: Rethink all stereotypes and assumptions about Americans, from impoverished Appalachia to a hippie commune in Tennessee.
12. Station Eleven by Emily St. John Mandel
How do you keep Shakespeare alive after the apocalypse? If you're The Traveling Symphony theatre company, just continue performing his plays across the wasteland and solving some bizarre mysteries along the way. Warning: This is not your average post-apocalyptic narrative.
I Spy: Cryptic tattoos, a prophet, bad dinner parties, divorce.
13. As I Lay Dying by William Faulkner
Or "How Not To Take A Family Road Trip."
What to pack: Embalming fluid, please. And some new mules. Also a fire extinguisher.
14. Flaming Iguanas by Erika Lopez
Lopez turns the "white man's road trip" trope on end with prose and illustrations so punchy that they barely stay on the page. Biker chicks, unite!
What to pack: A helmet. Maybe pants.
15. The Road by Cormac McCarthy
Any McCarthy will do, but this one has 'road' in the title and won the Pulitzer, so it's perfect! Also devastatingly haunting and spare.
I Spy: Concubines, cannibals, a can of Coke.
17. The Savage Detectives by Roberto Bolaño
The Savage Detectives is an ambitious modern epic, piling poetry, comedy, loss, sex, drugs, and forty(!) narrators into a globe-trotting journey that spans 30 years and nearly as many countries. It's not for the faint of heart, but a near-perfect meditation on the power and importance of art in the 20th century.
What to pack: Nametags.
18. Stranger On A Train by Jenny Diski
If you've never gone on a good, long train ride, here's your vicarious opt-in. Diski offers an outsider's (read: British) perspective on America's less-traveled tracks and the peculiar psychological idiosyncrasies of extended travel.
Watch out for: Lung cancer.
19. Lolita by Vladimir Nabokov
Okay, obviously there are a lot of things not to emulate here...but it's all about the journey, right?
Pit stops: Some caves, a couple fish hatcheries, Bourbon Street, Rocky Mountain National Park, a corn palace, too many motels.
20. The Electric Kool-Aid Acid Test by Tom Wolfe
What happens when you take Ken Kesey, some New Journalism, and a bunch of hippies and throw 'em all in a bus with a shit load of LSD? This hot mess of a masterpiece.
21. On Such A Full Sea by Chang-rae Lee
Speculative fiction at its — and Lee's — finest. Follow Fan, a skilled fish-tank diver from future-Baltimore, across anarchic and crime-ridden American hinterlands as she searches for her lover and inadvertently becomes a legend.
I Spy: Lush prose and freaky modern-day parallels.
22. A Brave Man Seven Storeys Tall by Will Chancellor
When an Olympics-bound Stanford water polo player suffers a career-ending injury, he does what anyone would do: flees the country to reinvent himself in an artist's enclave in Berlin. Along the way, we learn a lot about the classics, 1970s rock music, sheep farming, ophthalmology, family, and faith.
What to pack: Greek Mythology For Dummies, an eye patch.
23. Paper Towns by John Green
The master of the Bildungsroman delivers once again. Classic, un-put-down-able John Green.
1) Go on an adventure
2) Pull all the heartstrings
24. American Nomads by Richard Grant
This one basically does it all — you meet actual modern nomads, learn about the history of the American frontier, and see what it really means to wander.
People you'll meet: Drunk hitchhikers, methed-out cowboys, Álvar Núñez Cabeza de Vaca, RV people, etc.
25. Find Me by Laura van den Berg
Yes, it's another near-future post-apocalyptic pandemic-type story, but Van Den Berg's elegant prose and potent themes make this a worthwhile and enthralling read.
Pit stops: Abandonment, alienation, memory loss.
26. Angels by Denis Johnson
A perfect, rip-roaring ride across America's fringe — seedy bus stations and hotels included.
Brace yourself for: Too many hours on a Greyhound bus.
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The section on Reservation Blues has been edited for clarity and style.