The best books classic literary road trips worth reading

Linda Collison Author Of Looking for Redfeather
By Linda Collison

Who am I?

Somehow, I keep moving. I love going places and I love reading about explorers, itinerants, migrants, wanderers, and lost souls on the move. Looking for Redfeather started out as my National Novel Writing Month novel; the first draft, written in a mad dash during November 2007, when I was on the road, promoting my novel, Star-Crossed, a novel that also involves traveling. Looking for Redfeather was inspired by members of my own family—young people bent but not broken, malcontents on a mission, seeking something, but what? Published in 2013, it's a 21st century-coming-of-age road story, my tongue-in-cheek homage to Jack Kerouac, and the runaway teen still hiding out in my old soul.


I wrote...

Looking for Redfeather

By Linda Collison,

Book cover of Looking for Redfeather

What is my book about?

Fifteen-year-old Ramie Redfeather leaves Cheyenne with music in his pocket and his thumb in the air. He’s looking to find his father, a man he’s never met. Ramie gets a ride with Chas Sweeney, a seventeen-year-old driving a “borrowed” Cadillac Eldorado with Maryland tags, who happens to be passing through Cheyenne, on his way to Denver, running away from the wreckage that is his world, sixteen hundred miles away. In Denver, Ramie and Chas meet Mae B. LaRoux, an enchanting young singer from Baton Rouge. LaRoux, who struggles with a learning disability, is on a mission to become a professional musician. The three runaways band together and set out on a fast-paced road trip to get LaRoux to the Austin Music Festival, looking for Ramie’s father on the way. 

The books I picked & why

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On the Road

By Jack Kerouac,

Book cover of On the Road

Why this book?

On the Road is the mother of all 20th-century American road trips. It’s a mad rush West, an impetuous quest for life and friendship, as experienced by the protagonist, Sal Paradise. This is Kerouac’s episodic account of his own restless relationships among transients who question, postpone, reject, or can’t afford the post-World War II American dream of house, spouse, car, career, and kids. What I love about this iconic American road story is Kerouac’s authenticity, his thirst for life, his human fallibility, his truth. 

On the Road

By Jack Kerouac,

Why should I read it?

7 authors picked On the Road as one of their favorite books, and they share why you should read it.

What is this book about?

The legendary novel of freedom and the search for authenticity that defined a generation, now in a striking new Pengiun Classics Deluxe Edition

Inspired by Jack Kerouac's adventures with Neal Cassady, On the Road tells the story of two friends whose cross-country road trips are a quest for meaning and true experience. Written with a mixture of sad-eyed naivete and wild ambition and imbued with Kerouac's love of America, his compassion for humanity, and his sense of language as jazz, On the Road is the quintessential American vision of freedom and hope, a book that changed American literature and changed…


Zen and the Art of Motorcycle Maintenance: An Inquiry Into Values

By Robert M. Pirsig,

Book cover of Zen and the Art of Motorcycle Maintenance: An Inquiry Into Values

Why this book?

In the late 1960s, the author and his son ride a motorcycle across the Northwestern United States. At first it seems like a random, rambling sort of journey, but we soon discover Pirsig is on a mission to reconcile or reunite with a dark persona from the past, a man he calls Phaedrus. Persig uses the road trip as a framing device for his harrowing mental, emotional, and philosophical journey, and he takes us through some winding passages and desperate didactic encounters along the way, building tension like a thriller while giving a discourse in philosophy, questioning the meaning of insanity, and damning conventions of institutionalized academics. 

Zen and the Art of Motorcycle Maintenance: An Inquiry Into Values

By Robert M. Pirsig,

Why should I read it?

10 authors picked Zen and the Art of Motorcycle Maintenance as one of their favorite books, and they share why you should read it.

What is this book about?

Acclaimed as one of the most exciting books in the history of American letters, this modern epic became an instant bestseller upon publication in 1974, transforming a generation and continuing to inspire millions. A narration of a summer motorcycle trip undertaken by a father and his son, the book becomes a personal and philosophical odyssey into fundamental questions of how to live. Resonant with the confusions of existence, Zen and the Art of Motorcycle Maintenance is a touching and transcendent book of life.


Blue Highways: A Journey into America

By William Least Heat-Moon,

Book cover of Blue Highways: A Journey into America

Why this book?

If On the Road is a mad rush for connection, Blue Highways is a thoughtful professor’s journey on America’s back roads—represented by blue lines on 20th-century road maps. Much like John Steinbeck did twenty years earlier with his Travels with Charlie, William Least-Heat Moon takes to the road to discover 20th century America, reflecting the spirit of place and people, and how they are interconnected. Contrasted with Jack Kerouac—an impetuous young man thumbing his way across America on the “red line” highways—this mature writer explores the “blue line” back roads in his 1975 Ford Econoline van. Of English, Irish, and native Osage heritage, William Least-Heat Moon gives us an observant “deep map” American road trip worth taking.

Blue Highways: A Journey into America

By William Least Heat-Moon,

Why should I read it?

6 authors picked Blue Highways as one of their favorite books, and they share why you should read it.

What is this book about?

Hailed as a masterpiece of American travel writing, Blue Highways is an unforgettable journey along our nation's backroads.
William Least Heat-Moon set out with little more than the need to put home behind him and a sense of curiosity about "those little towns that get on the map -- if they get on at all -- only because some cartographer has a blank space to fill: Remote, Oregon; Simplicity, Virginia; New Freedom, Pennsylvania; New Hope, Tennessee; Why, Arizona; Whynot, Mississippi."
His adventures, his discoveries, and his recollections of the extraordinary people he encountered along the way amount to a revelation…


Travels With Max: In Search of Steinbeck's America Fifty Years Later

By Gregory Zeigler, David Swift (photographer),

Book cover of Travels With Max: In Search of Steinbeck's America Fifty Years Later

Why this book?

What are Americans like today? In the spirit of Travels with Charley, George Zeigler made his own journey in the early 21st century, retracing Steinbeck’s literary journey to rediscover his country. In the process, the Wyoming-based writer gives us not only a 21st-century road memoir, but a literary biography of America’s 1960 Nobel Laureate author. Gregory Zeigler explores the country to discover who Americans are today, and to pay homage to the great 20th-century novelist, John Steinbeck. “As for me, I got to know Steinbeck well and had one hell of an adventure following his tracks around the country,” Zeigler says. Makes me want to do the same.

Travels With Max: In Search of Steinbeck's America Fifty Years Later

By Gregory Zeigler, David Swift (photographer),

Why should I read it?

1 author picked Travels With Max as one of their favorite books, and they share why you should read it.

What is this book about?

Inspired by Travels with Charley, Gregory Zeigler celebrated the 50th anniversary of renowned Nobel Prize-winning author John Steinbeck's storied trip. In 2009, Zeigler and his dog Max drove and camped 15,000 miles over nine weeks, exploring the country and determining what Americans are like today. Travels With Max offers a retrospective on Steinbeck and his work, as well as an insightful, humorous and upbeat perspective on modern America.
Steinbeck's Travels with Charley will celebrate it's 60th anniversary in 2020.


Heroes of the Frontier

By Dave Eggers,

Book cover of Heroes of the Frontier

Why this book?

I’m a huge fan of Dave Eggers’ writing and Heroes of the Frontier was a bumpy back road into the wilds of Alaska and straight to my literary heart. His protagonist is a single mother on the lam from her ex-husband and leaving behind her profession, lost to a lawsuit. In spite of the character’s desperation, Eggers makes me laugh, he makes me cringe with embarrassment, he makes me feel like these characters are family. Like a real road trip, I sometimes found myself wondering Are we there yet? But I forgive him for the extra miles and all that time behind the wheel—the adventure and Eggers’ insights into contemporary American society were worth it. 

Heroes of the Frontier

By Dave Eggers,

Why should I read it?

1 author picked Heroes of the Frontier as one of their favorite books, and they share why you should read it.

What is this book about?

THE NEW YORK TIMES TOP 10 BESTSELLER

'The mirror image of Eggers's brilliantly dystopian The Circle... [A] state of the nation novel, cleansing the spirit and lifting the heart' Guardian

A hilarious and heart-warming misadventure through modern America: it's time for the family vacation...

Josie's life is falling apart - lawsuits raining down, her business down the drain and a feckless husband long gone - so she gathers up her two kids and lights out for the wilderness. The Alaskan wilderness, to be specific.

This is a story about the trip of a lifetime. It involves one battered old RV,…


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