2. Jack Kerouac, On the Road
Let’s get this one out of the way.
3. John Steinbeck, Travels with Charley: In Search of America
An American Institution travels the country in his later years, with poodle in tow? Hell yeah.
4. Denis Johnson, Train Dreams
A short, kinda lonesome book about a drifter-type character in the American West during the late 19th century. The prose is sparse, but it’s surprisingly emotional and poignant.
5. Joan Didion, The White Album
Wonderfully captures the creeping anxieties of life in California as the utopian dream of the ’60s flickered out.
6. Mark Twain, Life on the Mississippi
Who wouldn’t want to read Mark Twain write about his experience as a steamboat captain on the Mississippi river?
7. Tom Wolfe, The Electric Kool-Aid Acid Test
A seminal bit of New Journalism. Wolfe follows Ken Kesey and his LSD’d-out Merry Pranksters around the country.
8. William Least Heat-Moon, Blue Highways: A Journey Into America
“Blue highways” are non-interstate roads on older U.S. maps. Heat-Moon traveled these backroads to write about places like “Remote, Oregon; Simplicity, Virginia; New Freedom, Pennsylvania; New Hope, Tennessee; Why, Arizona; Whynot, Mississippi.”
9. Richard Brautigan, A Confederate General from Big Sur
Time this one with your drive up the California coast. A slightly meandering, almost absurdist tale with incredible imagery.
10. John McPhee, Coming into the Country
Okay, so not every U.S. road trip includes a drive through Alaska, but McPhee (a long revered New Yorker staff writer) has a meticulous and deeply engaging prose style.
11. Cheryl Strayed, Wild
A reflective and ultimately triumphant memoir about overcoming grief and “figuring it all out” that manages to avoid seeming self-indulgent or precious. The reviewer for the New York Times says it “pretty much obliterated [him].”
12. Larry Brown, Big Bad Love
Subtle, powerful, big-hearted short stories about Southern life with consistently magnetic characters.
13. Hunter S. Thompson, Fear and Loathing in Las Vegas
Drugs and visions and the desert and American mania and — most importantly — Thompson’s legendarily batshit prose-poetry.
14. Bonnie Jo Campbell, Once Upon a River
A sixteen year-old heroine sets out on a rural Michigan river. Harrowing and a full of wonderful details.
15. Richard Wright, Black Boy
Wright’s autobiography, with powerful portraits of both his childhood struggles in the racist south of the ’20s and his fitful political and intellectual awakenings after a move to Chicago.
16. Carl Sandburg, Harvest Poems: 1910-1960
Legendary critic H.L. Mencken called Sandburg “indubitably an American in every pulse-beat.”
17. Flannery O’Connor, A Good Man is Hard to Find
A stone-cold classic set of short stories that are dark and feverish and redemptive. Wrestles with that conflicted, twisted American moral compass.
18. Edward Abbey, Desert Solitaire
An impassioned paean to nature, framed around Abbey’s time as a park ranger in the Southwest.
19. Willa Cather, O Pioneers!
A turn of the century tale of Swedish immigrants in the American heartland. Manages to capture the epic sweep of America’s changing new frontier.
20. Sherman Alexie, Reservation Blues
Alexie’s writing is steeped in a very American brand of magical realism. Reservation Blues orbits around the legend of delta blues legend Robert Johnson and life on a Spokane Indian reservation.
21. Jon Krakauer, Into the Wild
A true tale of the “back to the land” dream gone terribly wrong. Fascinating reportage.
22. Chuck Klosterman, Killing Yourself to Live
The account of a road trip across America loosely organized around investigating the deaths of rock stars. Not everyone loves Klosterman’s goofily irreverent style, but Killing Yourself is an undeniably inventive modern American travelogue.
23. Bill Bryson, A Walk in the Woods: Rediscovering America on the Appalachian Trail
A love letter to some of America’s awe-inspiring natural beauty.
24. BONUS: Dashboard Books
Going cross country, the car is your home and the dashboard is your coffee table.
25. Robert Frank, The Americans
Frank traveled around America for two straight years (1955-57), taking nearly 28,000 photos in the process. The result is maybe the most definitive snapshot of the country and its citizens in their own time.
See some of the photos here.