(Credit: Francisco Gonzalez / Alamy / Wikimedia)


On The Road: Follow in the footsteps of Jack Kerouac’s American road trip


“Nothing behind me, everything in front of me, as is ever so on the road.” – Jack Kerouac

Now that the dust has settled on Jack Kerouac’s blustering travels, it has not only become clear that he is America’s true luminous literary nomad, but also, with 1957’s On The Road, he may well have penned the most seminal novel of the 20th Century. Open any given modern copy, and you may well find Bob Dylan printed into the sleeve proclaiming, “It changed my life, like it changed everyone else’s.” Or perhaps it will be some other beatnik-spawn, proudly eulogising the trail that his life-giving prose blazed through the malaise of static predestined existence, bursting into bloom a bright new bohemian future for a thousand-fold army of disenfranchised youth aiming to tackle things a little differently from their forebearers. Their mantra seemingly: if we are to fail, then so be it, at least we did it on our own wavering terms. 

How, then, did his book prove so influential? Well, there are no doubt a myriad of reasons – the fickle fate of circumstance being one of them – but aside from that, what is obvious to observe is that it offered up the presentiment of a vibrant life beyond banality in a pretty monochrome world at the time. Aside from the endless misreadings, the scoffs of cynics and the analysis of its place in literature, the simple brooding pleasure of On The Road resides in the joy of life in motion and all the technicolour tones that whiz by. In short, the eternal duck soup thrill of a road trip. 

Since 1957, this presentiment has never lost its appeal. There is simply something truly cathartic about setting off in a car and soundtracking an adventure that not even the blight of cheesy auto-generated Instagram quotes can besmirch. In Kerouac’s golden prose, he hightails his way through the high and lows, trials and tribulations, vistas and moments of effortless victory. As he journeys his way between the amassing concrete sprawl of America to the last green wildernesses and back to the boom of some happening city once more, he refuels and revels. Though the spaces may be smaller these days, that adventure is still there to be plundered, as our guide will show.

Much like Kerouac’s trip, it will be more so rough seas than plain sailing. It will be pitted with moments of deep regret as you wake up hungover in some nowhere town that offers up none of the quaint charms that the imagination offered. You might misplace your wallet and face a moment of utter doom-laid despair and fear at times that scurvy has taken hold, but the life-affirming boon of the flipside will mean that it will forever be worth it and offer up constant reminders of that.

The Jack Kerouac Road Trip:

New York 

I was beginning to get the bug like Dean. He was simply a youth tremendously excited with life, and though he was a con-man, he was only conning because he wanted so much to live and to get involved with people who would otherwise pay no attention to him.

Getting there…

In Kerouac’s circular loop of America, New York was the start, finish and spiritual home. It was here that the beat generation was formed, and it was in the borough of Greenwich Village that those that crawled from the pages of Kerouac would set up their Gingham-clad home. Getting there is easy, of course, as the Big Apple is one of the best-connected cities on the planet. 

To see and do…

In On The Road, the touchstone of New York is the hive of art on which the trip is centred, and while not all the jazz clubs, Harlem joints and playhouses are still standing, plenty of the beat spirit remains. Harlem clubs like the throwback Lenox Lounge that welcomed the incomparable air of Billie Holliday in 1939 and still sees her sultry class linger like a numen, is a must-see beat joint; while Barbès of Brooklyn offers up a more casual modern equivalent. 

The essential spot, however, will forever be on the trail of the generation that followed. The legacy of Kerouac still lingers strongest in the hub of his disciples amid the bohemian Greenwich Village and the emblematic Village Vanguard club, open since 1935 and still welcoming patrons into its folky bebop vibe for very attainable fees. And en route, it’s worth walking just a mile through the treelined thoroughfares to reach Kerouac’s old abode at 454 West 20th Street, where, in a fevered frenzy fuelled by God knows what, he cracked out On The Road in around three weeks flat. 

The Village Vanguard at night, 1976. (Credit: Tom Marcello)


“Great Chicago glowed red before our eyes. We were suddenly on Madison Street among hordes of hobos, some of them sprawled out on the street with their feet on the curb, hundreds of others milling in the doorways of saloons and alleys.”

Getting there…

The drive from New York to Chicago is an 800-mile affair, passing thorough Pennsylvania and the old gawping scenery of the imposing Great Lakes. Then as it was in Kerouac’s day, the city emerges from the banks of the water like a candle to the moth of your trail. 

To see and do…

While Kerouac’s intro to the windy city might focus on its rough and tumble underbelly, he is nevertheless beguiled by its blustering charm and earthly hum. Nowhere is the happening vibe felt more fervently than in the “screeching trolleys, newsboys, gals cutting by, the smell of fried food and beer in the air, neons winking”, and everything else that the kaleidoscopic Loop district is awash with. Sadly, The Loop bears little resemblance now to the one that Kerouac immortalised, but the great Millennium Park in summer is still very much worth a glossy-eyed trip.

The Uptown district, however, is where his words still register. In jazz bars like Green Mill, The Welcome Back Lounge and many more, the heady bustle of jazz, blues, booze and big smoke is bountiful. And at cheaper rates than New York, you can afford to make it a sleepless city before venturing from the dive bar din back into “the great roar of Chicago… to sleep until the wild bop night again’.”

(Credit: Nima Sarram)

New Orleans

“Once there was Louis Armstrong blowing his beautiful top in the muds of New Orleans; before him the mad musicians who had paraded on official days and broke up their Sousa marches into ragtime. Then there was swing, and Roy Eldridge, vigorous and virile, blasting the horn for everything it had in waves of power and logic and subtlety—leaning into it with glittering eyes and a lovely smile and sending it out broadcast to rock the jazz world.”

Getting there…

While some may wish to skip New Orleans simply in favour of a straighter path, others will be welcomed at the end of their wavering near-thousand-mile journey to a place that befittingly the boom of modern popular art began. Jazz, blues, and rock ‘n’ roll came roaring from the swirled mixing bowl of the Delta South, with its crooked tupelo trees, serpentine dust roads and the giant clay ball moon that seems to be a few miles closer to the delta than the rest of the world, presiding in the hot sultry evening air. In fact, you can even visit Congo Square, where modern music began.

To see and do…

On route, the delta opens up before you, in the words of Paul Simon, like the National Guitar, to the old chic city hive where Bob Dylan pined for his euphoric ‘evening’s empire’ not to ‘vanish into dust’. In a place where Louis Armstrong heard the sound of the future come billowing around the corner out of Buddy Bolden’s mythologised horn. Bars, clubs and street names may have changed since, but there is an atmosphere in the city that will no doubt prove eternal. 

In the old crooked French Quarter, the quirky world that Kerouac relished remains bustling with jazz and blues aplenty. Snug Harbour, Lafitte’s Blacksmith Shop Bar, Erin Rose and Elizabeth’s all offer up the timeless appeal of dizzy nights with cool sweat in your hair and never a dull sight for the eyes to see. Likewise, the cafés by day, like Monty’s on the Square, offer a breezy spot of tranquilly to take it all in through weary peepers, with the peace of the Garden District always awaiting a trip. 

The French Quarter, New Orleans. (Credit: Pixabay)


“I pictured myself in a Denver bar that night, with all the gang, and in their eyes 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!”

Getting there…

Denver is the spot that Kerouac perhaps visits most in his unfurling journey through the “great rolling bulge of the West”. It comes at the end of a mammoth 1400 miles stretch through the South, but, along the way, the true remnants of small-town America remain, and curious sites keep the often flat roads interesting in realms often unchartered by what might be considered mainstream American imagery. 

There was a time when Denver was a cultural hub akin to New York as the jazz scene boomed back in the day. And while the frontier mining origins that caused the brand-new weekend city to blaze like a beacon for tired travellers back in the day might have been modernised, the scenery surrounding it remains as striking and stirring as ever. For this alone, it is still more than worth a visit; after all, what is the point of a road trip if not for the journey?

To see and do…

Upon arrival, the city also still keeps some of its old famous jazz joints secret. Don’s Club Tavern, where various On The Road scenes unspool, is a relic as pristine as any on your time following the trail of the beats. And thanks to the relatively smaller size of the city, El Chapultepec is another quintessential jazz joint from the book that can be visited in the same night of nostalgic reverie amid the mountain air. Even historic hotels like Brown Palace can provide a bed and some long-awaited luxury for a fee that shouldn’t totally destroy the bank. 

(Credit: Onetwo1)

San Francisco

“It seemed like a matter of minutes when we began rolling in the foothills before Oakland and suddenly reached a height and saw stretched out ahead of us the fabulous white city of San Francisco on her eleven mystic hills with the blue Pacific and its advancing wall of potato-patch fog beyond, and smoke and goldenness of the late afternoon of time.”

Getting there…

The route to San Fransico allows for two divergences worth taking; one through Yellow Stone in the north before heading back down to the Salt Flats in the south then on through Nevada to one of America’s greatest cities, not only cherished by Kerouac but just about every visitor – San Francisco. If you head straight there from Denver, it’s about 1300 miles, but if you weave through the National Parks, you can add on many more… all of which are worthy. 

To see and do…

Of all the cities on his seminal journey, in San Fran’, it’s like stepping back into the pages of his eulogising prose. “Old ‘Frisco with end of land sadness,” Kerouac regales regarding life in ’50s California, “Nobody knew or far from cared who I was all my life, 3500 miles from birth all opened up and at last belonged to me in great America.” In the sweeping rush of the American boom, he saw both the beauty and the lamentable elements of people getting busy “with not even enough time to be disdainful,” in the opening piece of his own jazz album ‘October in the Railroad Earth’.

This mixed-up milieu still exists. While the city may have its issues with homelessness, its charms, for the most part, remain. Here you can find just about everything he mentions still intact, thriving, and barely tainted by time. There’s even a Beat Museum that proves well worth visiting; in fact, there are so many Kerouacian sites to see that they warrant a separate piece of their own, like the Big Sur chronicle to his life on the road.