Tracing America’s Iconic Literary Road Trips
From Lewis and Clark’s expedition to the Pacific to Hunter S. Thompson’s hallucinated Vegas detour, the American road trip has long served as both a literal journey and a metaphorical one—a vehicle for discovery, reinvention, rebellion, and reflection. These stories span centuries and styles, yet each captures a distinct moment in time and place: whether it’s Steinbeck searching for the soul of a changing nation, Kerouac chasing the sublime across dark and distant highways, or Fitzgerald sputtering south in a doomed jalopy with Zelda.
Undaunted Courage: Meriwether Lewis, Thomas Jefferson, and the Opening of the American West by Stephen E. Ambrose (1924)
“But his fixed rule was always to assume the road ahead was good, until proved otherwise.”
Undaunted Courage by Stephen Ambrose chronicles the epic, cross-country expedition of Meriwether Lewis and William Clark as they lead the Corps of Discovery from St. Louis to the Pacific Ocean and back. Traversing untamed rivers, towering mountain ranges, and vast plains, the journey offers a sweeping portrait of early 19th-century America. And although not depicting a road trip per se, at its heart, this book conveys a vivid account of exploration, ambition, and the raw, often perilous reality of charting a new nation’s path westward.
Route: St. Louis → Kansas → Iowa → South Dakota → North Dakota → Montana → Idaho → Washington → Oregon
The Cruise of the Rolling Junk by F. Scott Fitzgerald (1924)
“There was a certain zest in being out of touch with the world, in taking chances and trying to make the old car go just one more mile.”
In the summer of 1920, shortly after their marriage, Scott and Zelda Fitzgerald decide to drive from Westport, Connecticut, to Montgomery, Alabama, to visit Zelda’s family. Their vehicle: a 1918 secondhand automobile—a true “rolling junk”—that is already prone to overheating, sputtering, and falling apart before they even leave the driveway. What follows is a delightfully chaotic road trip through Pennsylvania coal country, the rolling hills of Virginia, the Carolinas, and down into Georgia and Alabama—punctuated by mechanical failures, strange lodgings, and Fitzgerald’s sharp-eyed, often bemused reflections on a rapidly changing America.
Route: Connecticut → New York City → Philadelphia → Washington D.C. → Virginia → The Carolinas → Montgomery, Alabama
Car Name: Rolling Junk
On The Road by Jack Kerouac (1951)
“There was nowhere to go but everywhere, so just keep on rolling under the stars.”
Possibly the most well-known and well-loved road trip novel of all time, On The Road is Jack Kerouac’s frenetic, semi-autobiographical chronicle of cross-country road trips taken by Sal Paradise and his magnetic, reckless friend Dean Moriarty in search of meaning, freedom, and experience. As they crisscross postwar America—from the jazz clubs of New Orleans to the plains of Nebraska—Kerouac captures the restless spirit of a generation chasing the sublime through highways, strangers, and the endless promise of the open road.
Route: New York → Chicago → Des Moines → Denver → Cheyenne → Salt Lake City → San Francisco
Travels with Charley by John Steinbeck (1961)
“I saw in their eyes something I was to see over and over in every part of the nation—a burning desire to go, to move, to get under way, anyplace, away from any Here.”
In 1960, John Steinbeck set out with his poodle, Charley, on a cross-country journey to rediscover America. Driving a custom camper named Rocinante, he traveled through small towns, big landscapes, and quiet highways, encountering a nation both familiar and strange. Along the way, he reflected on identity, change, and the contradictions at the heart of American life.
Route: Sag Harbor, NY → Connecticut → Maine → North Dakota → Yellowstone National Park → Seattle → New Orleans → Sag Harbor, NY
Truck Name: Rocinante (after Don Quixote’s horse)
Fear and Loathing in Las Vegas by Hunter S. Thompson (1971)
“Every trip to Las Vegas was a carefully planned and totally crazy adventure.”
In perhaps his most famous novel, Hunter S. Thompson writes about a journalist named Raoul Duke and his attorney, Dr. Gonzo, embarking on a drug-fueled road trip to Las Vegas under the pretense of covering a desert motorcycle race. What begins as an assignment quickly unravels into a surreal, chaotic odyssey through casinos, hallucinations, and existential despair, as the pair seek out the real meaning behind the American Dream as the 1960s come to close.
Route: Los Angeles → Las Vegas → Los Angeles
Blue Highways by William Least Heat-Moon (1982)
“I took to the open road in search of places where change did not mean ruin and where time and men and deeds connected.”
Blue Highways is a novel by William Least Heat-Moon that documents his journey driving across the United States using only backroads and secondary highways, often marked in blue on old maps. Following the loss of his job and the end of his marriage, Heat-Moon sets out in a van to explore small towns and rural communities, aiming to better understand the country and its people.
Route: Missouri → Nameless, Tennessee → Louisiana → Texas → New Mexico → PNW → Montana → Midwest → New England → West Virginia
Truck Name: Ghost Dancing
Black, White and The Grey: The Story of an Unexpected Friendship and a Beloved Restaurant by Mashama Bailey and John O. Morisano (2021)
“When Morisano first walked me through the old terminal, he paused and pointed toward the back near the restrooms. “That was where the colored waiting room was,” he said matter-of-factly. I stopped in my tracks. “Excuse me—wait, what?” I replied, stunned. It still existed—dusty, faded, spurring an almost eerie awareness of the building’s segregation-era history.”
In Black, White, and The Grey, restaurateurs Mashama Bailey and John O. Morisano recount the road trip that sparked their unlikely partnership—an odyssey from New York to Savannah that forced honest conversations about race, identity, and trust. Their journey becomes a vehicle for exploring personal history and cultural divides, setting the stage for building The Grey, a restaurant that reimagines Southern hospitality in the bones of a once-segregated Greyhound station.
Route: NYC → Virginia → The Carolinas → Savannah, Georgia
These literary road trips continue to inspire the journeys we design for our clients—everything from a guided river expedition down the Missouri, a culinary pilgrimage through the South, or a nostalgic drive along the cliffs of Big Sur.
If you’re ready to start planning yours—we’re here to make it happen.
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