…what are they and what did you take away from reading them?
Assuming you mean books about road trips, and not specifically to read while on one, I would think Blue Highways by William Least-Heat Moon is really high up on the list for “must read.” It took me three times to start reading and finally get into it, but I came to really love it about a quarter into it. It was written 30 years ago, so I liked reading about what the US was like shortly before I was born, and it simply did a good job of taking me places I’ve yet to go. I’ve spent next to no time in New England and the Deep South, so he painted pictures to help me besides the images I can find in a Google image search. I don’t remember anything being particularly profound, but I really felt like I was with him throughout.
The only problem is that, shortly after reading Blue Highways, I read a Bill Bryson about his road trip throughout the US, though in the late-80s, and trying to recall specifics of who went to this state or that has left my memory a bit off. And I’d recommend the Bryson book, too. It’s called The Lost Continent: Travels in Small-Town America. Bryson’s book is more humorous, but there’s more depth to Least-Heat Moon’s.
Jack Kerouac’s On the Road is an absolute classic of the genre although by this point it’s as much a historic snapshot of the era as it is a great read. Many of Kerouac’s other works involve road trips too like The Dharma Bums and Desolation Angels to name a couple.
Tom Wolfe’s =The Electric Kool-Aid Acid Test is another must-read even if it’s a bit different than most road trips, although perhaps it’s a road “trip” in another sense.
Zen and the Art of Motorcycle Maintenance by Robert M. Persig is another one to get although I enjoyed it much less than most of Kerouac’s work or the Electric Kool-Aid Acid Test.
I should also mention the great John Steinbeck. You’ve probably heard of The Grapes of Wrath, but his lesser-known Travels with Charley is very enjoyable indeed.
One thing that sets all these books apart for me is that they’re as much social commentary as they are adventure stories. When I first read On the Road as a young man, this book broadened my horizons a great deal and led me to other works such as David Riesman’s The Lonely Crowd. While this may seem outdated today, in the early 1980s it felt as relevant to me as critics acclaimed it when first published.
Bri2k
Three of my favorites are:
On the Road----Jack Kerouac
Been Down So Long it Looks Like Up to Me----Richard Farina
Fear and Loathing in Las Vegas----Hunter S. Thompson
They span “my time” for me.
(I liked Dharma Bums, too. Not so much the Zen of Mortorcycle Maintainence.)
Lolita, after Charlotte dies, is mostly road trip. Beautifully written and funny.
Opened the thread to say exactly that.
Not exactly a “road-trip book”, but many years ago I read “The Odyssey” while on my first real road-trip. It was actually pretty comforting. “If Odysseus could get where he was going” I thought, “than I can too”.
Like Becky2844, one of my favorite “road-trip” books would have to be “Fear and Loathing In L.A.”
I really liked the one paragraph where Thompson describes seeing the exact moment when the 1960’s failed. He was using a metaphor of a wave sweeping in or something like that (I don’t have my copy with me so this is all from memory). It was a very poignant moment in an otherwise chaotic book.
I found Neil Peart’s Ghost Rider to be captivating. It’s Peart’s moving description of a months-long motorcycle trip throughout the western hemisphere in the wake of the deaths of his daughter and his wife.
I may find this book more appealing than some because I am a) a huge fan of Rush (Peart is Rush’s longtime drummer) and b) I am a devoted motorcycle touring enthusiast. But it’s a very good story about life and loss and healing.
I quite like Grapes of Wrath too.
So did I. Even though it’s the equivalent of “I only read it for the articles…”
The Size of the World by Jeff Greenwald
Jeff Greenwald, travel writer, realizes that he has completely lost touch with how the world is really experienced by the 90% of the world’s population that can’t afford air travel. He decides (publisher’s advance in hand) to circumnavigate the globe with no airplanes. On foot, by car, by train, by boat, by donkey, but no airplanes.
Really really well written with funny parts and scary parts and introspective parts and sad parts.
A memorable part is getting a visa to go through Saudi Arabia (apparently not an option if you are A. a writer and B. jewish). Lies are told, pleas are made, but finally it all comes down to the pigeon phobia of a kind low level Saudi diplomat.
Road Fever by Tim Cahill.
My takeaway from reading the book: don’t settle for instant coffee on long drives. 
The Greatest Thing Since Sliced Bread by Don Robertson. A 12-year-old boy sets out (with his wagon) on a journey across Cleveland to visit a friend who moved away. I’m always amazed at authors who can get back into their childhood selves. Robertson is one of my favorite writers. Most of his stuff is out of print, but this one’s been brought back.
Also The Widows’ Adventures by Charles Dickinson. Two older women, traveling to California to visit relatives. What’s unusual is that the only one of the women who know how to operate a car is blind – she drives, while the other pilots. Gimmicky, but that part takes a back seat (har!) to their story, as they consider their lives, and where they belong.
I really like Dickinson. He wrote a cracklin’ good time travel novel called A Shortcut in Time. It needs a sequel and he’s written it but his publisher doesn’t want it. 