The road trip is one of the great tropes in storytelling.
The desire to leave home for an extended journey on the road can be found in stories from nearly every culture throughout history. While the locations and time periods may change, the themes are often very similar: escape, adventure, personal and spiritual growth, or something as simple as just needing a good burger.
For this article we selected 20 epic road trip stories from books and films, and then dug into the Shutterstock collection to find 100 images inspired by these stories. Spoilers ahead!
The Odyssey – Homer
“A man who has been through bitter experiences and travelled far enjoys even his sufferings after a time”
Homer’s pre-Christian epic adventure saga is one of the oldest surviving pieces of narrative fiction in the world, but it’s rarely featured on great road trip rundowns. To be sure, ancient greek poetry is outside the norm for the road trip genre, but on his 10-year journey home from Troy to Syracuse, Odysseus and his crew encounter a slew of misadventures and setbacks that go to show that The Odyssey might be the boilerplate for the road trip genre, as well as all of Western literature.
On the Road – Jack Kerouac
“Nothing behind me, everything ahead of me, as is ever so on the road.”
On the Road is perhaps one of the most celebrated and widely recognizable pieces of writing to emerge from the Beat Generation, following the semi-autobiographical travels of “Sal Paradise” and his pal Dean Moriarty across the vast cultural landscape of 1950’s America. On the Road is the story of a trip without a destination, an exploration of the American spirit during a time of shifting national identity and an exaltation of the untethered lifestyle lead by Kerouac and his fellow Beats.
Motorcycle Diaries – Che Guevara
“I now know, by an almost fatalistic conformity with the facts, that my destiny is to travel…”
The published diaries of one of the most polarizing figures of the latter half of the 20th century shed light on the real man, Ernesto “Che” Guevara, whose face has become synonymous with protest and revolution. Documenting his travels with friend Alberto Granado first-hand, The Motorcycle Diaries are far from the buoyant hijinks commonly associated with road trips. Rather, they show the political and philosophical evolution of one of the most influential figures in recent memory as he travels by dirt bike through the impoverished communities of Latin America.
The Americans – Robert Frank
“Above all, life for a photographer cannot be a matter of indifference”
Armed with a Guggenheim Grant, swiss-born Robert Frank set out on a road trip across the United States to photograph American people of all economic strata in an unflinching, candid way. His subsequent book, The Americans went on to become one of the most influential photography books in the history of the medium and created a template for road trip books that generations of photographers have looked to for inspiration.
Fear & Loathing in Las Vegas – Hunter S. Thompson
“Too weird to live, too rare to die.”
Written in Thompson’s signature style of gonzo journalism, Fear & Loathing is the surreal account of a debauched, drug-addled road trip through the American Southwest, culminating in Sin City itself. The story’s subtitle “A Savage Journey to the Heart of the American Dream” is truly ironic, as journalist Duke confronts the collapse of the counterculture and the beginning of the ideologically confused 1970s.
Sleeping by the Mississippi – Alec Soth
“….storytelling is the most powerful art, for me. I just think there’s nothing more satisfying than the narrative thrust: beginning, middle, and end, what’s gonna happen.”
Magnum photographer and Minnesota native Alec Soth burst onto the photography scene with his now classic debut book Sleeping by the Mississippi, in which 46 large format photographs set a mood of loneliness and reverie through an eclectic mix of people, landscapes, and interiors from the geography around Midwest America’s most prominent body of water. The success of the book has influenced countless photographers to take up large format photography and hit the road seeking their own Mississippi.
Eat, Pray, Love – Elizabeth Gilbert
“The only thing more unthinkable than leaving was staying; the only thing more impossible than staying was leaving.”
After a contentious divorce, writer Elizabeth Gilbert set out on a journey of healing and redemption, traveling to Italy to indulge in the pleasures of food and conversation, then off to India seeking the divine through prayer, and finally to Bali to unify the two. Oh, and she happened to fall in love along the way. The book was so popular it was turned into a film starring Academy Award winner Julia Roberts.
Tracks – Robyn Davidson
“And here I was at the end of my trip, with everything just as fuzzy and unreal as the beginning.”
In 1977 writer Robyn Davidson set out on an epic 1,700 mile journey across the Australian outback with four camels and a dog in a spiritual quest to understand the harsh landscape and Aboriginal people that inhabit it. Along the way she fought off poisonous snakes, endured the sweltering heat, nursed her injured camels, was joined by a National Geographic Photographer, suffered the death of her dog, became a media sensation, and eventually completed her transformative journey with a new love of the outback. You can get this story served up on film as well, in a 2013 adaptation starring Mia Wasikowska.
Wild – Cheryl Strayed
“I’d finally come to understand what it had been: a yearning for a way out, when actually what I had wanted to find was a way in.”
Four years after her mother’s death from cancer and the dissolution of her marriage, 26 year old Cheryl Strayed decided to take a hike. With no previous hiking experience, she ended up on month long journey of self-discovery along the Pacific Coast Trail. The subsequent book tells of her physical and emotional challenges along her path of self-discovery. Here’s another book you can opt to watch, with Reese Witherspoon playing the part of Strayed (and trekking her way to an Academy Award nomination).
Anywhere But Here by Mona Simpson
“Be optimistic, don’t be so grumpy, when the road gets bumpy, just smile, smile, smile, be optimistic.”
In her debut 1987 novel, Mona Simpson tells the story of a tumultuous Mother-daughter relationship as they leave their small Wisconsin town with dreams of making it big in Hollywood. Frequently fighting on their journey, the duo navigate their competing ambitions by learning to accept each other’s flaws.
National Lampoon’s Vacation
“When I was a boy, just about every summer we’d take a vacation. And you know, in 18 years, we never had fun.”
The American family vacation is ripe territory for an outrageous road trip, and perhaps no film has exploited that potential more than National Lampoon’s Vacation. The Griswold family journey from Chicago to Walley World in Los Angeles is filled with memorable mishaps, including a visit to Uncle Eddy’s strange family, a dead grandmother on top of an Oldsmobile, and an unforgettable encounter with a blond bombshell in a red Ferrari. The Griswold’s demonstrate that even the boring old family vacation can turn into an epic road trip.
“They’ll talk to ya and talk to ya and talk to ya about individual freedom. But they see a free individual, it’s gonna scare ’em.”
An On the Road-like story for the freewheeling, free-loving hippy generation, Easy Rider captured the existential angst of a counter-culture in decline. The film follows two hog-riding hippy pals played by Peter Fonda and Dennis Hopper as they cruise through the American South on a mission of spiritual truth-seeking. Ultimately, they uncover a country in conflict with itself and are forced to wonder whether the hippie style de vie can survive in this new America.
Thelma & Louise
“Driiive Louise! Drive! Drive the car! Go! Go! Go go go go go go!”
One of the appeals of the road trip narrative is the unpredictability it brings into the characters’ lives. Thelma and Louise set out on a weekend trip to escape their monotonous lives and unattentive boyfriends. When they stop at a roadside bar for a drink, the story takes a tragic turn after Louise kills a man who attempts to rape Thelma, setting off a classic police chase as they make a run for the Mexican border. Their tragic ending has become embedded in pop culture memory.
“Try to be your normal, humorous self. The guy you were before the tailspin. Do you remember that guy? People love that guy.”
The road trip is often cast as the remedy to youthful restlessness and the answer to adolescent soul-searching. The 2004 dramedy Sideways, starring Paul Giamatti, substitutes a mid-life crisis for the typical youthful rumspringa. The film combines wry humour and West Coast wine snobbery, resulting in a funny and touching take on the road trip template.
Little Miss Sunshine
“A real loser is someone who’s so afraid of not winning he doesn’t even try.”
The dysfunctional Hoover family is on a mission to get seven-year-old Olive from Albuquerque to Redondo Beach so she can participate in the Little Miss Sunshine pageant. They pack into an old yellow VW minibus and hit the open road, trying to reach the pageant on time while surviving each other. It’s a hilarious and often touching family journey that culminates with Olive and the family embracing their inner ‘Super Freak.’
Harold and Kumar Go To White Castle
“I am so hungry. I’m gonna eat, like, 20 of those burgers, man.”
Sometimes a road trip has a very simple goal, and for stoners like accountant Harold and medical student Kumar, that goal is sliders from White Castle. It can never be that easy though, and in this stoner road comedy our heroes face many hilarious obstacles in their pursuit of mini burgers, including an angry raccoon, a kinky Freakshow, a pothead Cheetah, and a car-stealing Neil Patrick Harris high on ecstasy (who ultimately saves the day).
“I’m flying high over Tupelo, Mississippi… with America’s hottest band… and we’re all about to die.”
For many rebellious teenagers, going on the road with their favorite rock band is the ultimate dream, symbolic of freedom and excitement. In 1973, 15-year-old William aspires to be a music writer and ends up landing his dream assignment with Rolling Stone, which allows him to follow the up-and-coming band Stillwater. During William’s journey, he learns about the drama that follows rock bands, as well as what it takes to be a writer and tell an authentic story. With the help of a charming groupie named Penny, he’s ultimately able to write the story he wants to write.
Sisterhood of the Traveling Pants
“Wear them. They’ll make you brave.”
As four lifelong friends on the cusp of adulthood are about to strike out on their own separate paths for the summer, they come across a choice piece of denim that will serve to preserve their friendship across oceans and continents. First written as a series of hugely popular teen novels before becoming a string of equally successful silver screen adaptations, Sisterhood doesn’t strictly adhere to the conventions of the road trip format, but nonetheless embodies the themes of kinship, adventure, and coming of age better than any story about pants ever written.
The Darjeeling Limited
“I wonder if the three of us would’ve been friends in real life. Not as brothers, but as people.”
From the mind of visionary director Wes Anderson comes the story of three estranged and emotionally distant brothers reunited on a trans-Indian railroad journey to visit their self-exiled mother in a Himalayan convent. Though more of rail trip than a road trip, strictly speaking, The Darjeeling Limited is an exemplary dissection of relationships, family and spirituality in our consumer-driven century, all while covering quite a few kilometers of adventure-laden Indian countryside in the process.
Life of Pi
“For castaways who must share their lifeboats with large, dangerous carnivores, it is advisable to establish a territory as your own.”
Legendary Director Ang Lee’s adaptation of this fantasy adventure novel finds teenager Pi stranded at sea with a Bengal tiger, a zebra, and an orangutan after the freighter his family chartered to transport the animals from their zoo in India sinks. This sets off a fantastical odyssey of survival, hardship, and friendship at high sea. Along the way, Pi encounters a majestic humpback whale, a floating island of interconnected trees, and a colony of meerkats before eventually reaching the coast of Mexico where he must convince insurance agents that his story is true.
See more images inspired by pop culture’s greatest road trips in the Stories from the Road curated collection: