On the Road

“We packed my brother’s furniture in back of the car and took off at dark promising to be back in thirty hours–thirty hours for a thousand miles north and south. But that’s the way Dean wanted it.”

Jack Kerouac, On the Road
I feel like if you own a copy of this book and it’s not worn and battered, you’re doing it wrong.

Book Info

Author: Jack Kerouac

Published: 1957

Geographic Area: The United States, with a little bit of Mexico

Original Language: English


I found On the Road at the perfect time in my life. It was 2008, I was a sophomore in high school, and I got bit hard by the wanderlust bug. I would have trouble sleeping, so I’d sneak out of the house in the middle of the night and just go for a walk. I wouldn’t go far back then, staying within the bounds of my suburban hometown, but what mattered was that I was going somewhere. There were a lot of problems at home, and so not only did I like being away from the house, but the simple process of being in motion helped me deal with my anxiety.

I don’t remember if I first heard of the book from my parents, or from my English teacher, Mr. Doyle, or if it’s just one of those pop culture things that percolates down to you at some random interval. Either way, I knew immediately that I had to buy it. I picked it up from my neighborhood Barnes & Noble and, 307 pages later, I knew I had just read one of the most influential books of my entire life.

On the Road was published in the late-’50s, but actually chronicles a series of cross-country road trips taken a decade prior. The book begins with the author finding himself heavily depressed following a divorce. Befriending the free-spirited and hedonistic Dean Moriarty, Kerouac finds renewed interest in life. Thus begins what he calls his “life on the road.”

He sets out from New York City in 1947, in a pair of huarache sandals, with several notebooks in his bag and $50 in his pocket. Over the next four years, he takes us on an epic road trip of the United States, years before the advent of the Interstate Highway System. We witness his experiences from the backseats of old hot rods, from the insides of Greyhound buses, and from the beds of pickup trucks hurtling through the night in the Deep South. Along with Dean and several other companions, they go out to San Francisco by way of Denver, Los Angeles by way of New Orleans, across America’s Heartland, and even down into Mexico. Along the way he presents an intimate look at the “beat generation,” as well as firsthand accounts of the people, cities, and music of post-war America. He works various jobs, such as a nightwatchman at an army barracks, and a laborer in the cotton fields. He leaves all of these–as well as a family–opting instead to get back on the open road.

Let me be clear about something here. I recommend this book as an inspiration for just getting in your car and going somewhere on a free weekend. I do not recommend this book as justification for being completely laissez-faire about your responsibilities, which is what a lot of these guys were. Even Kerouac does not paint a particularly likable portrait of himself; depressed about a divorce at the start of these adventures, he finds himself going through another by the novel’s end.

You can think of the “beat generation” as a sort of spiritual precursor to the hippies. The beats, or beatniks, were perhaps less about drug use (although you will find plenty of that in this book) or free love (there’s a lot of that, too), instead aspiring to be more of a logical, intellectual group of poets and artists.

Dean Moriarty on the left, Jack Kerouac on the right.

Many historians agree that Jack Kerouac was not so much a beatnik himself, but more of a chronicler of the beatniks. Born in Lowell, MA in 1922, he found himself involved with the beat generation as a young man. Several of the most prominent beat writers of the time, such as Allen Ginsberg and William S. Burroughs, make appearances in On the Road, albeit under aliases: “Carlo Marx” and “Old Bull Lee,” respectively. In fact, Kerouac himself goes by “Sal Paradise.” Dean Moriarity’s real name was Neal Cassady.

Several years back, I had the pleasure of attending an exhibit on Jack Kerouac at the Harry Ransom Center in Austin, TX. It was there that I learned that the original manuscript of On the Road was written over the course of three weeks on one very long scroll of linotype paper.

Not only is that a neat little fun fact, but it’s also important to keep in mind when you read this work. The events are presented in a stream of consciousness style. It can get kind of wild. It does not have the more formal prose that you may expect from Paul Theroux or Jon Krakauer. I can guarantee you that much if not all of it was typed up while under the influence of narcotics.

Yes, the characters are not perfect human beings. Yes, the writing style can take some getting used to. But I feel like that’s exactly what gives this work such a unique personality, and makes it one of the most greatest travel books of all time.

You can find an interactive map of Kerouac’s road trips here.


If you like, you can purchase a copy of On the Road by clicking the image below. Just so you know, this is an affiliate link, so if you choose to make a purchase, I get a small percentage.

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