The American road trip is as old as the country itself. Early in our history the road trip was embodied by the desire to head west, leave civilization and explore new lands. It meant freedom and opportunity. Yet like most countries, we continue to move towards more settling, more civilization, ever-expanding suburbs and strip malls. But there have always been discontents; those unsatisfied with the creature comforts of society, those who see true freedom as available only while on the move. Or maybe view life on the road as a way to find themselves, or find purpose, or to heal. Whatever their motivation, many of these people recorded the tales of their adventures on the road. Whether you are looking for inspiration, answers, motivation, or just a good story, these are the best American road trip books.
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Blue Highways by William Least Heat-Moon
“There are two kinds of adventurers: those who go truly hoping to find adventure and those who go secretly hoping they won’t.”
The plan: “to set out on a long (equivalent to half the circumference of the earth), circular trip over the back roads of the United States. Following a circle would give a purpose — to come around again — where taking a straight line would not. And I was going to do it by living out of the back end of a truck.” The idea came, Heat-Moon says, in the middle of the night, February 17th, a day of “canceled expectations”. After finding out his job teaching English had been cancelled. After calling his wife, with whom he had been separated for nine months, to tell her the news and finding out about her “friend — Rick or Dick or Chick. Something like that.” And thus was born the plan. And one of the best American road trip books of all time.
A month later, at 38 years old, Heat-Moon set out in his truck in search of the back roads and small towns of America. “With a nearly desperate sense of isolation and a growing suspicion that I lived in an alien land, I took to the open road in search of places where change did not mean ruin and where time and men and deeds connected.” What follows is a masterpiece of American travel writing.
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The power lies in Heat-Moon’s stepping aside and letting those he meets tell their stories. Americans thougth to no longer exist, true originals, whose stories capture an America only found in the forgotten towns. Michael Parfit of the LA Times had this to say: “Heat-Moon walks through this book about our land and our people with a patient, eloquent, beautiful pace, his eyes taking in everything and it’s meaning. Then he puts our words and our vistas into language that lives on the page.” Our favorite of the best American road trip books and a must-read for those embarking on a trip of their own.
Our favorite quotes from Blue Highways:
“A rule of the blue road: Be careful going in search of adventure — it’s ridiculously easy to find.”
“City people don’t think anything important happens in a place like Dime Box. And usually it doesn’t, unless you call conflict important. Or love or babies or dying.”
“My rambling metaphysics was getting caught in the trap of reducing experience to coherence and meaning, letting the perplexity of things disrupt the joy in their mystery. To insist that diligent thought would bring an understanding of change was to limit life to the comprehensible.”
“If the circle had come full turn, I hadn’t. I can’t say, over the miles, that I had learned what I had wanted to know because I hadn’t known what I wanted to know. But I did learn what I didn’t know I wanted to know.”
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On the Road by Jack Kerouac
“I first met Dean not long after my wife and I split up. I had just gotten over a serious illness that I won’t bother to talk about, except that it had something to do with the miserably weary split-up and my feeling that everything was dead. With the coming of Dean Moriarty began the part of my life you could call my life on the road.” In On the Road Jack Kerouac tells the story of Sal Paradise following his hero, Dean Moriarty, around the country. They experience underground America: sex, jazz, drugs, and the open road. Sal sees Dean as “in possession of the key to unlock the door to the mysterious possibilities and richness of experience itself.” It’s a book that Kerouac once described as “a novel whose background is the recurrence of the pioneering instinct in American life and its expression in the migration of the present generation.”
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The book was an instant hit, deemed to channel the voice of the Beat generation and challenge the “complacency and prosperity of postwar America.” And yet, as William Burroughs said about it, “You can’t tell anybody anything he doesn’t know already. The alienation, the restlessness, the dissatisfaction were already there waiting when Kerouac pointed out the road.” Exploring themes of “personal freedom” while it also “challenges the promise of the ‘American dream’”. Possibly the most iconic American road trip of all time and a clear choice for our list of best American road trip books.
Our favorite quotes from On The Road:
“We were all delighted, we all realized we were leaving confusion and nonsense behind and performing our one and noble function of the time, move. And we moved!”
“And [Dean] stood swaying in the middle of the room, eating his cake and and looking at everyone with awe. He turned and looked around behind him. Everything amazed him, everything he saw. People talked in groups all around the room, and he said, ‘Yes! That’s right!’”
“‘Sal, we gotta go and never stop going till we get there.’
‘Where we going, man?’
‘I don’t know but we gotta go.’”
“Dean took out other pictures. I realized these were all the snapshots which our children would look at someday with wonder, thinking their parents had lived smooth, well-ordered, stabilized-within-the-photo lives and got up in the morning to walk proudly on the sidewalks of life, never dreaming the raggedy madness and riot of our actual lives, our actual night, the hell of it, the senseless nightmare road. All of it inside endless and beginningless emptiness. Pitiful forms of ignorance.”
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Travels with Charley: In Search of America by John Steinbeck
“When I was very young and the urge to be someplace else was on me, I was assured by mature people that maturity would cure this itch. When years described me as mature, the remedy prescribed was middle age. In middle age I was assured that greater age would calm my fever and now that I am fifty-eight perhaps senility will do the job. Nothing has worked.” And so begins John Steinbeck’s journey across America to “rediscover the country he had been writing about for so many years.” Bringing along Charley, his French poodle, Steinbeck starts in Northern Maine and crosses the country to Monterey, CA and then back again to his home in New York. What results is one of the best American road trip books ever written.
Written in 1962, Steinbeck was at the time a well-renowned and successful author—in fact he won the Nobel Prize the same year. Despite having written about America and its inhabitants for over 30 years, Steinbeck writes in the beginning of Travels with Charley, “I discovered that I did not know my own country. I, an American writer, writing about America, was working from memory, and the memory is at best a faulty, warpy reservoir.” And Steinbeck discovers America, in only a way he can. From truck drivers, to bears, to French migrant workers, and some old friends in San Francisco, he tells the stories of people who you would never hear about otherwise. A legendary writer goes on a journey and creates one of the very best American road trip books ever.
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Our favorite quotes from Travels with Charley:
“The techniques of opening conversation are universal. I knew long ago and rediscovered that the best way to attract attention, help, and conversation is to be lost. A man who seeing his mother starving to death on a path kicks her in the stomach to clear the way, will cheerfully devote several hours of his time giving wrong directions to a total stranger who claims to be lost.”
“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…I saw this look and heard this yearning everywhere in every state I visited. Nearly every American hungers to move.”
“I wonder why it is that when I plan a route too carefully, it goes to pieces, whereas if I blunder along in blissful ignorance aimed in a fancied direction I get through with no trouble.”
“When the virus of restlessness begins to take possession of a wayward man, and the road away from Here seems broad and straight and sweet, the victim must first find in himself a good and sufficient reason for going. This to the practical bum is not difficult. He has a built-in garden of reasons to choose from.”
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American Nomads by Richard Grant
“Lurking in the American psyche, however, there exists an entirely different conception of liberty, with no roots in European political philosophy. We might summarize it as a nomad’s creed: that freedom is impossible and meaningless within the confines of sedentary society, that the only true freedom is the freedom to roam across the land, beholden to no one.”
In American Nomads, Richard Grant explores this conception of freedom in American history, from conquistadors, to cowboys, to modern day truck drivers. He follows the history of the American nomad and looks at the myths and realities of living a wandering life. He combines this with stories and experiences from his own American travels: “Looking back at my own American wanderings, they seem to flow together as one; memories strung out on a single cord of highway, fourteen years long and headed nowhere in particular…My plan was to live this way for the rest of my life. Wandering became a manifesto, an obsession, a solution to all problems. Possessions were a pointless encumbrance, ambition was a trap, mortgages were obscene…and romantic entanglements were something to be wary of.” A clear recipe for the creation of one of the very best American road trip books.
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Combining his own experience with those from American history, Grant expertly captures the feelings so many Americans have about living on the road, being free, travelling from place to place. He explores the view of the civilized and sedentary, and their romanticizing of the nomad—how consumerist America envies the nomad, and yet are unwilling to give up their creature comforts and live a life of hardship and freedom. After extensive research, Grant ultimately concludes by quoting Rudyard Kipling, “When all is said and done, there are two types of [people]: those who stay at home and those who do not.” American Nomads is a must read for fans of the best American road trip books.
Our favorite quotes from American Nomads:
“I like to think I have tasted freedom, but I also recognize the signs and snares of addiction. After a while, wandering generates its own momentum, its own set of cravings, phobias and justifications. I like to think of it as an adventure, a perpetual seeking out of new horizons and experiences, but like so many endeavors of this kind, it has also been an act of flight—away from a point in space and time, away from routines and responsibilities, away from a state of mind. And when it began, escape was my only concern.”
“Bad planning is the mother of adventure.”
“In America you grow up with that cowboy ideal, that you should be independent and self-reliant and value your freedom above all else. That’s what the films, and TV, and books, and popular culture tell you American is all about. Then you find out that, in reality, society wants you to be exactly the opposite: obedient, fearful, dependent, basically a good little wage slave.”
“How tragic it is that so many people in the world will never see a night sky like this, will go to their graves without seeing the Milky Way. And how pleasant that none of them are around tonight.”
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Any books you think we should add to our list of the best American road trip books? Any of your favorites that we left out? Comment below and let us know what your list of the best American road trip books would look like!
