How Jack Kerouac is still shaping the great American road trip


My personal commemoration of Jack Kerouac happens every time I pick up a rental car in the United States. I always feel anxious behind an unfamiliar steering wheel. It takes me a while to get comfortable with the idiosyncrasies of a new ignition, locate the cap of the petrol tank and figure out how to operate its wing mirrors. You have to negotiate the exit ramp, find your way to the downtown of an unfamiliar city, not stall or get shouted at, and keep to the right-hand side of the road. 

That is a lot to think about, particularly after a long-haul flight. Summoning the spirit of Kerouac, a can-do pioneer, an adventurer, an evangelist for petrol-powered motion, calms me. It’s about the journey ahead! Neuroses begone! “Come on,” I tell myself. “Lean forward to the next crazy venture beneath the skies! The road is life!”

Few people have written so intoxicatingly about the magic of the open road, the romance of driving, the life-changing possibilities of travel as Kerouac, born 100 years ago today. The shadows of Kerouac and his real-life driving buddy Neal Cassady hang over every American road trip. On The Road, finally published in 1957, almost 10 years after the journeys it celebrates, made its 35-year-old author famous as the spokesman of the Beat Generation and a bard of the US highway. 

utah american road trip jack kerouac

Hit the road, Jack: a drive through the open landscapes of Utah has become an American classic

Credit: Getty

But before any know-it-all reader points out the irony, let me do it first: Kerouac didn’t learn to drive until after On The Road was written and he never had an actual licence. Sal Paradise, his alter ego in the fictionalised version of his adventures on the tarmac may share the driving with Dean Moriarty, but in real life, Jack was only qualified to be in charge of snacks and map-reading.

I was a non-driver when I first read On The Road as a teenager. The novel was one of those cult books like Catcher in the Rye, Zen and the Art of Motorcycle Maintenance and Steppenwolf, which were passed reverentially between enthusiasts and seemed to promise to induct you into a secret brotherhood. It didn’t hurt that Kerouac and his wing-man and mentor, Cassady – renamed Moriarty in the book – were handsome. 

I made my own pilgrimage to the Beat Museum in San Francisco a few years ago. It’s located close to the city’s big Chinatown and a short walk from Jack Kerouac Alley. It has an odd selection of exhibits. Among them are one of Kerouac’s plaid shirts, the kitchen table from Cassady’s San Francisco apartment and photos of the men looking like Gap adverts in chinos and white T-shirts. 

It reminds you how the cult of personality is an intrinsic part of the Beats’ appeal. However much you admire the prose of Ian McEwan or Hilary Mantel, you’re unlikely to covet their underwear. The museum’s centrepiece is a 1949 Hudson, a gas-guzzling monster with vast seats, just like the one Cassady bought for their journeys on the road. 

beat museum san francisco

The 1949 Hudson at the Beat Museum in San Francisco

Credit: Dennis Hearne

Reading the book for the first time in the 1980s, I was struck, as everyone is, by its rhythmic, celebratory prose and the freedoms – some of them still taboo – that it embraced: drinking, nightclubs, jazz, marijuana, free love, even a little light recreational car theft. 

Most of all, it made me long to hit the road myself. And looking back I see that the itineraries of my subsequent journeys followed routes first scouted out by Paradise and Moriarty: west to California from New York through the gold-rush towns of the Rockies; a loop through the desert south-west; the straight shot from wintry New York to the swampy heat of New Orleans; and a long drive south from Denver to the Mexican border and across.

new orleans jack kerouac road trip

New Orleans: ‘The air was so sweet in New Orleans it seemed to come in soft bandannas and you could smell the river and really smell the people, and mud, and molasses, and every kind of tropical exhalation with your nose suddenly removed from the dry ices of a Northern winter’

Credit: William Widmer / Redux / eyevine/Redux / eyevine

I also felt a personal kinship with Kerouac that strengthened my feeling of his significance. The child of French-Canadian immigrants to the United States, Kerouac grew up in Lowell, Massachusetts, and his first language was strongly accented québécois, with its rolled Rs and stock of bizarre Catholic profanities: “Tabernacle!”, “Chalice!”, “Sacrament!”

The diaspora of French-Canadians in the mill towns of the US north-east is a tiny disregarded part of America’s cultural gumbo, but it’s part of my heritage too. My grandfather, Albert Theroux, shared an almost identical family background with Kerouac, who was more than 10 years younger. And in the late 1940s, when Kerouac was undertaking the journeys that would become central to his myth, my grandfather was also on the road – as a salesman for the American Oak Leather Company. 

This is as far as the comparison goes. Albert was an upstanding family man, hardworking, reliable and God-fearing. Kerouac and Cassady would have probably found him a contemptible square. Albert once called up a radio station to complain about the lyrics of an Ervin Drake song they were playing, which he felt were in poor taste. The song is in fact a pretty accurate precis of the plot – in so far as it has one – of On The Road. It goes “I fell in with evil companions/The things that they did were a crime/The girls they pursued were shockingly rude/ And I had a wonderful time.”

Rereading On The Road for Kerouac’s centenary, I found that the book was very different from my recollection of it. I thought it was going to be a straightforward clenched-fist salute to the joys of the road. In fact, it is sadder, more tormented, and more relentlessly male than I had remembered. I also noticed that in the intervening years my sensibility has grown away from Kerouac’s and towards my grandfather’s. The book’s self-absorption grates. The male characters sometimes seem cruel and entitled. 

Jack Kerouac beat generation

All that jazz: Kerouac became a spokesman of the Beat Generation

Credit: JERRY YULSMAN/Associated Press

Kerouac’s stabs at Blakean profundity often come across as silly and sophomoric. “I would be strange and ragged and like the Prophet who has walked across the land to bring the dark Word, and the only Word I had was ‘Wow!’” 

At the same time, On The Road possesses an undeniable energy, and despite its many faults, it still kindles a desire to be on the road again. It is filled with a hunger for experiences, a desire to wring the most out of life. And this appetite is contagious. Enthusiasm – passionate, irony-free and often over-the-top – is the book’s cardinal virtue. “I kind of liked him,” Kerouac says of someone in the novel, “not because he was a good sort, as he later proved to be, but because he was enthusiastic about things.” 

Although it’s billed as a novel, On The Road essentially records four long journeys across America that Kerouac undertook under the inspiration of his muse and idol, Cassady. The latter was a fast-talking, handsome, charismatic young man, five years Kerouac’s junior, who’d spent time homeless and in juvenile prison. His worldliness, his patter, his years of precocious vagrancy made a huge impact on Kerouac, whose father had died shortly before. To Kerouac, Cassady seemed to be a shaman-like figure who possessed the secret to some transcendental joy. 

hollywood california jack kerouac on the road

Hollywood: ‘I looked greedily out the window: stucco houses and palms and drive-ins, the whole mad thing, the ragged promised land, the fantastic end of America’

Credit: Getty

Inspired by his encounter with Cassady/Moriarty, Kerouac’s alter ego begins a series of journeys in 1947, lighting out into an America that’s on the verge of an extraordinary economic expansion. He’s blithely unaware of it, but one of the things that makes his trips possible is the post-war boom. He stumbles into offers of work wherever he goes. For a time he’s a guard in a barracks for overseas construction workers. He picks cotton and works in a fruit market. Moriarty, meanwhile, gets jobs on the railways, in a tyre factory and as a sales rep for a pressure cooker company. 

One benign surprise is that the gas-guzzling 1949 Hudson doesn’t actually appear until halfway through the novel. Moriarty is able to buy it new with money from his railroad job. But even when the two men can’t afford a car of their own, they’re able to borrow them. During this period, wealthy Americans who couldn’t be bothered to drive long distances deposited vehicles at travel bureaus for other people to drive for them. In this way, Paradise and Moriarty find themselves the custodians of an almost-new Cadillac limousine in Denver: “The owner had been driving up from Mexico with his family and got tired and put them all on a train.” 

If the owner had had any inkling about who was going to end up behind the wheel, he might have had second thoughts. Moriarty drives so fast, the speedometer breaks and he trashes the car on the way to Chicago. His driving is so wayward that Paradise can’t even watch. This is one of those moments where, reading the book as a parent, you feel Moriarty is precisely the kind of friend you don’t want for your children. And in fact, despite Paradise’s blind worship of him, the novel’s women see him with bitter clarity: “You see what a bastard he is?” one of his girlfriend’s warns Paradise. “Dean will leave you out in the cold any time it’s in his interest.” “You have absolutely no regard for anybody but yourself and your damn kicks,” another character tells Moriarty.

Kerouac doesn’t appear to see it, but Paradise and Moriarty’s journeys ultimately founder on selfishness and their inability to look after each other. There is a lot of mutual admiration, but a lack of care. This gives the story its bipolar rhythm: manic enthusiasm for a new destination, followed by defeat, hunger, exhaustion, and often a falling-out. 

Each time, the road that has seemed so promising becomes “a senseless nightmare road” and Paradise heads back to Long Island to be with his aunt. It’s too bad that Kerouac didn’t give the unvarnished version of this. He actually lived with his mum, and went home to be with her. It would have been brave to reflect this truthfully, but presumably the bathos of going home to Mum risked being fatal to the myth.

Still, anyone who has driven for any length in the US will recognise the accuracy of Kerouac’s descriptions and share his excitement at the prospect of the unfolding journeys. His book is, among many things, a hymn of praise to the possibilities of forward momentum, and the openness of the American landscape. 

What gives it power is the vividness of his recollections. The legendary account of Kerouac transcribing the novel onto a roll of paper during three Benzedrine-fuelled weeks of frantic typing obscures how carefully remembered each portion of the journey is. He recalls the place names, the weather, the details of sunrises, the idiosyncratic comments of his chance companions.

Kerouac flits between New York, Denver and Chicago: “Screeching trolleys, newsboys, gals cutting by, the smell of fried food and beer in the air, neons winking – ‘We’re in the big town, Sal! Whooee!’” He heads south to Louisiana and Mexico. He zips across the Midwest and spends weeks in southern California. He crosses the vast spaces of Texas: “Now we were on the great Texas plain and, as Dean said, ‘You drive and drive and you’re still in Texas tomorrow night.’” He travels through railroad yards, mountain passes, cities at night, bars, and the fog-bound streets of San Francisco, for which he has a special affinity: “The fabulous white city of San Francisco on her 11 mystic hills with the blue Pacific and its advancing wall of potato patch fog beyond, and smoke and goldenness in the late afternoon of time.”

chicago jack kerouac american road trip

Chicago: ‘Screeching trolleys, newsboys, gals cutting by, the smell of fried food and beer in the air, neons winking – “We’re in the big town, Sal! Whooee!”’

Credit: Getty

The economic optimism that sustains Paradise and Moriarty’s wild ride has sadly gone. The jazz clubs that they venerate are no more, no one calls marijuana “tea”, and bebop is not the cutting edge of contemporary music. But youth has the same idealism and self-regard and the same contempt for the values of its elders. Watching the Battersea-born pianist George Shearing tear loose in a New York jazz club, Kerouac reassures us: “These were his great 1949 days, before he became cool and commercial.” 

And 70 years after the journeys it records, much of what Kerouac sees is still recognisable to a traveller. Licence or no licence, his spirit continues to offer a reassuring backslap to a nervous driver and extend an eternal invitation to readers to get behind the wheel of a car and see America for themselves.

3 trips to feel like you’re On The Road 

Though endlessly evocative on the page, the journeys around America detailed in On The Road are largely meandering affairs that are not easily reprised as holidays unless you have the same swaths of time to play with and a similar instinct for the unbeaten track. But while several niche places – St Louis, Cincinnati, Texas’s south-western borderlands – crop up in Kerouac’s text, three key cities have a special presence. Each can be the basis for a road trip in 2022.


In some ways, the Colorado capital is a metropolis alone – famously marooned at altitude, with the Rocky Mountains rearing to the west. Kerouac visited it en route to California. Modern tourists should use it as a starting point for a journey that goes in search of the state’s rugged majesty, whether that be the grand groove in the ground that is Black Canyon of the Gunnison (, or railroad town Durango, where the Durango & Silverton Railroad ( still forces steam-powered passage through San Juan National Forest.

Bon Voyage (0800 316 3012; offers Colorado, Mountain Country & the Mother Road, a 14-night odyssey that calls on all the above locations, as well as the state’s second city, Colorado Springs. From £2,095pp, with flights

San Francisco

California’s great city on the bay is On The Road’s pot of gold, siren-calling to Kerouac from his life in New York. It needs scant introduction: the Golden Gate Bridge is an unmistakable icon, the bars and restaurants of the Mission District are lively. But San Francisco will always lend itself to wider adventures, whether (like the author) you go south to LA, or east into nature, taking in the peaks and waterfalls of Yosemite National Park (, or the heat of Death Valley (

Complete North America (0115 961 0590; offers a California Sunshine Coast from San Francisco trip that takes 15 days over its progress to San Diego, via Monterey, Santa Barbara and LA. From £2,199pp, with flights

golden gate bridge sf

A view of the Golden Gate from Fort Baker

Credit: Getty

New Orleans

Kerouac has some of his wildest encounters in the second part of On The Road, swapping New York for the Algiers district of New Orleans. Three-quarters of a century later, the most fabled dot on the map of Louisiana is still a splendid soup of a city – sticky under foot in the watering holes of the French Quarter, much more authentic in the music clubs on Frenchmen Street in Faubourg Marigny. Its decadent air can be compelling, but also exhausting. Once you’ve had your fill, drive out to explore a state alive with Creole soul.

The 14-night Louisiana’s Finest fly-drive offered by America As You Like It (020 8742 8299; also trundles into the state capital Baton Rouge, and dips into neighbouring Mississippi. From £1,509pp, flights included

Chris Leadbeater

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