Summer is the time for road trips: that great, glorious, ridiculously inefficient way of getting from Point A to Point B. A road trip, by its very nature, invites segues, detours, sidequests, and lollygagging. When you embark on a road trip, expect the unexpected.
A road trip is also a perfect vehicle for a story: It’s an amazing way to express both an inner and an outer journey — to track progress in a plot and also in a character. And the trip doesn’t have to be conventional — your vehicle can be anything from a wheelbarrow to a rocketship, and your destination anywhere from the next state over to the next galaxy.
If you’re ready for some of the greatest, and strangest road trips of your life, from Ithaca to Mordor, read on.
The Odyssey by Homer
Possibly the road trip. Also, the reigning champion for the longest time taken to road trip on this list, and maybe of all time. Join Odysseus on a decades-long quest just to get back home to his wife and kid, which for some reason involves witches, sirens, whirlpools, and a nearly all-powerful goddess.
If The Odyssey were an actual road trip, it would be like getting from Connecticut to Vancouver by way of Panama, Hawaii, and the North Pole. Odysseus may not be the most efficient, but it makes for fantastic character development, and, you know, the foundation of Western narrative storytelling.
Raw Dog by Jamie Loftus
If you’ve ever daydreamed about road tripping across the entire United States while taste testing hot dogs from every region, and also experiencing personal turmoil to varying levels, then boy, do I have the book for you. Jamie Loftus lives the dream, and lived to tell us about it in Raw Dog, a road trip book if there ever was a road trip book.
Raw Dog’s road trip is pretty much confined to America, but it will make you feel every emotion from mild nausea to nostalgia to slight melancholy, which is everything a road trip really should be.
Station Eleven by Emily St John Mandel
Set in a post-pandemic world and starring a troupe of Shakespearean actors who caravan around the Great Lakes region of North America, on a sort of perpetual road trip, Station Eleven is like a retro-dystopia, while also a prescient look at how thoroughly a pandemic might change society.
Emily St John Mandel writes with remarkable clarity, making even the prospect of a world at the end of civilization one replete with hope and possibility, as much as it also inspires fear. As the characters’ paths and lives intersect and connect with one another, their love for the written word and its power shines through.
On The Road by Jack Kerouac
Jack Kerouac’s iconic road trip memoir conveys the frenetic, chaotic nature of the time he lived in, where one could hitchhike across the United States, ping-ponging between cities and people as easy as breathing.
On The Road chronicles the Beat Generation’s ethos and a series of road trips that Keruoac describes as being usually spur-of-the-moment, after he’s bitten by the “bug.” From New Orleans to Virginia to New York to Los Angeles, by bus, car, and train, Sal Paradise does it all, and you can be along for the ride.
Howl’s Moving Castle by Diana Wynne Jones
Diana Wynne Jones’ fantasy novel, which inspired the iconic Studio Ghibli movie, includes potentially the most unique of the vehicles on this list. Wizard Howl’s behemoth of a castle, which roams around and also somehow exists in multiple places at once, is something that could only exist in the fantasy world of Ingary.
Sophie and Howl also cover a lot of ground in their endless road trip, crossing continents and even exploring parallel dimensions, bickering all the while, before eventually finding their way back to the castle and each other.
Mosquitoland by David Arnold
Mim Malone’s journey home from Mississippi to Cleveland Ohio is a classic road trip journey. Motivated by her desire to see her mother again, Mim cobbles together a journey by bus back to her hometown. Of course, she is met with plenty of quirky characters, setbacks, and detours along the way.
Mim’s modern-day odyssey may be shorter than some of the other trips on this list, but through her eyes, the reader understands how monumental this trip is for her. This journey is sometimes funny, occasionally emotional, and always honest, like all the best road trips.
The Two Towers by J.R.R. Tolkien
Imagine a road trip without cars or other forms of motorized transport — horrible. Now imagine a road trip into the heart of the most evil sorcerer your world has seen, possibly ever. And Gollum is also there. You now have some idea of what Frodo and Sam experience in The Two Towers.
Journeying into the middle of Mordor certainly comes with a higher-than-average level of risk for creepy crawlies and encounters with the enemy, but this road trip has stakes that are ridiculously high, so even the boring parts come with a good amount of nail-biting tension. Also, Sam and Gollum hating each other with a passion is wildly entertaining.
Whether you came for descriptions of cities and the feelings of progress, melancholy, and contemplation that a road trip can stir up, or you’re here for the ways the journey mirrors a character’s traits and arc, there’s sure to be a book on this list that revs your engine.
After all, as these books can attest, it’s not exactly about where you’re going — New York, Ithaca, or the fires of Mordor — but about the friends you make, and the experiences you have, along the way.
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