Kerouac’s masterpiece On The Road is based on wild, improvised trips he took across the US. Follow in his footsteps to the five cities that kept calling him back.

The USA is a big country. And whenever anyone’s tried to define – be they a Charles Dickens, a Mark Twain or a Stephen Fry – it they’ve hit the road. So did the Beat Generation, a group of 1940s university students in New York. They’d skip class to dig jazz and debate their place in Cold War America. And then they’d hit the road: crisscrossing the country in search of the new American dream – or just for kicks, music and women.

The Beat bible, if there is one, is On the Road, Jack Kerouac’s mostly autobiographical novel about a series of aimless road trips taken from 1947 to 1950. It’s now a Hollywood production: Walter Salles’ film is out this autumn.

Kerouac appears as the book’s narrator, Sal Paradise.  Other key Beats make the novel too, including the poet Allen Ginsberg and novelist William S Burroughs. The hero is Dean Moriarty, based on Neal Cassady, a Coloradoan who marks his trips with a ‘wild yea-saying overburst of American joy’.

Can you travel the road in that same spirit today? Kerouac tried in 1960, and failed, finding that interstates had come, bypassing many of the towns that he’d torn through a decade before. But if the Beats can teach us anything about travel, it’s that every journey presents new opportunities. Here are five key cities to visit, places that Kerouac knew and that still inspire the ‘bug’ that drew him across the country more than 60 years ago.

New York: The start and finish of a Beat Generation trip
New York is the city that never sleeps – and it was particularly awake after WWII. Wall Street boomed, the United Nations picked a Manhattan spot on the East River as its base, and developer Robert Moses lit a fuse on city projects that created the skyline that is so familiar to us today. It was in this New York that the Beat Generation was born, with students dropping out of college and experimenting with drugs, music, sex and literature in a quest to find an alternative to the rampant, materialist lifestyles that they saw growing around them.

 It is also where Kerouac’s novel begins and ends. In On the Road, it was a place of jazz clubs and diners, of trips taken on the A-train and long nights spent at dingy taverns, surrounded by ‘the absolute madness and fantastic hoorair of New York with its millions and millions hustling forever for a buck among themselves’. It was in Harlem jazz joints such as Minton’s Playhouse that fast-tempo bebop developed out of old-school jazz. Kerouac was such a bebop fan that trumpeter Dizzy Gillespie named a 1941 song after him, and ‘bop’ soon became the soundtrack for the Beats alongside more traditional jazz.

Though Minton’s is now closed barring the odd jazz festival, you can still find plenty of vintage variety in late-night joints. Harlem’s Lenox Lounge is a 1939 club where Billie Holiday played, and Brooklyn’s Barbès serves up cocktails and bourbon alongside its music performances. But the essential Beat stop is the time-warp basement venue of the Village Vanguard in Greenwich Village, open since 1935. Kerouac performed jazz poetry here in the 1960s, not long after he lamented that ‘jazz is killing itself here’ because of its high cover prices. It’s hard to complain about the $25 admission fee these days when you can encounter real bebop survivors like 82-year-old jazz pianist Barry Harris, who did a two-week stint here last summer.

Kerouac lived just under a mile away at 454 West 20th Street in the 1950s, banging out the first draft of On the Road in three weeks. His manuscript consisted of a single paragraph on a continuous 120-foot scroll of paper; it sold at auction for just under £1.5 million in 2001, and was finally published in its original form by Penguin in 2007 (£10.99). When not at his desk, Kerouac hung out with Allen Ginsberg at the 19th-century White Horse Tavern (567 Hudson Street, 00 1 212 989 3956), made infamous as the site of Dylan Thomas’s fatal drinking binge in 1953. The pub has since become a West Village institution, popular now with locals, literary students and curious tourists alike.

On the Road’s own melancholy end comes after a newly married Sal Paradise decides to settle down in New York, after zigzagging across the USA in a whirl of mayhem with Dean Moriarty. Sal waves goodbye to the itinerant Dean from a Cadillac window as he heads up West 20th Street to Penn Station and the train that will carry him west. Afterwards, Sal sits on an ‘old broken-down pier’ on the Hudson River and watches the sun set. It’s hard to know which pier he sat on, but a good proxy is the Hudson River Park, stretching up the west side of Manhattan and lined with bike paths, two landscaped piers and the odd café. It’s especially lovely at the end of the day, so do as Sal did: watch the sun go down in ‘the long, long skies over New Jersey’ and ‘all that raw land that rolls in one unbelievable huge bulge over to the West Coast, and all that road going, all the people dreaming in the immensity of it’.

Book one of the six characterful rooms at the Sankofa Aban b&b, located in a four-storey brownstone building in Brooklyn and dating back to the 1880s. It hosts jazz concerts on Friday nights (from £95).

Chicago: The Beats meet the Mob in the Windy City
Chicago ‘glowed red’ when Sal and Dean pull into the city in On the Road. Kerouac describes it as a ‘semi-Eastern, semi- Western’ city – and it’s that midway location that transformed it in the late 1800s as America’s railroad hub, a position it would hold for 100 years. The two protagonists arrive not by train but in a borrowed Cadillac that they proceed to smash up as they zip madly from club to club, bar to bar, in search of good times and girls.

They divide their time between the historic Loop district, on the edge of Lake Michigan, and Uptown, further north. In On the Road, the Loop was all ‘screeching trolleys, newsboys, gals cutting by, the smell of fried food and beer in the air, neons winking’. While its Theater District has retained the neon, the Loop has changed immeasurably since the mid-20th century. The area is now home to Chicago’s financial district as well as museums, galleries and Millennium Park, with artworks including Anish Kapoor’s Bean, and free summer concerts. There is little of Kerouac to find here, though, considering his brief stint with the US Navy, you could get your 21st-century kicks at popular Navy Pier, a distracting bevvy of fast-food restaurants and high-tech amusement rides. There are free firework displays from the pier on summer evenings.

 Musically, Chicago is best known for its blues, but Sal and Dean came to ‘see the hootchy-kootchy joints and hear the bop’. They spend the night following musicians into unnamed saloons and drinking beer until nine the following morning. You’ll get kicked out at 4am but, to re-create some of the spirit of their night, head over to Green Mill. It has been the place to go for drinks and jazz in Uptown Chicago for over a century, and was one of Al Capone’s favourite clubs. In its 1920s heyday, it filled a block-long complex that included theatres and restaurants. It still retains its original feel – past the entrance with its sparkling lights lies a true cocktail lounge, with curved leather booths and bar tenders’ colourful tales about the mobsters who owned shares in the place. A trapdoor behind the bar leads to tunnels where they hid their bootlegged booze. When singer Joe E Lewis refused to play the Green Mill, he got his throat slashed. He survived the attack, then agreed to play. Today, jazz is played nightly, and willingly – afterwards, stagger out ‘into the great roar of Chicago... to sleep until the wild bop night again’.

Recover from your revelry in a smart room at the Wyndham Blake Chicago, housed in the old customs building in the Loop (from £145).

Chicago is 20 hours from New York by train (from £65); 13.5 hours (800 miles) by car; or a 90-minute flight (from £60).

New Orleans: Ferry rides and good times in the Deep South
New Orleans ‘burned in our brains’, writes Kerouac, as Sal and Dean are drawn south by the promise of the ‘greeneries and river smells’ of the city that’s regarded as the birthplace of jazz. Driving down the Gulf Coast, they click on a local Chicken Jazz’n Gumbo radio show (WWOZ is a nice proxy), Dean yelling out of the car window, ‘“Now we're going to get our kicks!”’

Yet, instead of jumping into the fray, they catch the ferry to Algiers, a sleepy neighbourhood across the Mississippi. Algiers felt like a deserted island in the 1940s. It’s still pretty removed, with quiet blocks of century-old shotgun shacks. But you should at least ride the ferry across Ol’ Man River, which has run here since 1827. It’s free for pedestrians, and can be at its most atmospheric at night, the time when Sal watches the ‘mystic wraith of fog over the brown waters’.

Sal and Dean stay in Algiers with Beat writer William S Burroughs (Old Bull Lee in the book), who lives with his family and seven cats in a ‘dilapidated old heap with sagging porches’. He doesn’t much like New Orleans – the one night they hit the French Quarter, Old Bull purposely takes them to dull bars. The district deserves more consideration; while Bourbon Street gets all the attention for its touristy nightlife, you're never far from quiet streets full of 19th-century townhouses, housing art galleries and Creole restaurants. For bigger kicks, Kerouac would have enjoyed Frenchmen Street, steps east from the French Quarter. Just walk up it and listen out for the music you want to hear, diving in and out of local bars and cafés. A stand-out, and frequently dubbed the best jazz venue in the city, is the intimate Snug Harbor, a brick-wall venue in a converted townhouse. Sal’s lingering memory of New Orleans is the sweet smell of its air, its river, its people and its mud; add the smell of meat loaf, BBQ and po’boys to the mix at Elizabeth’s. One of New Orlean’s favourite down-home restaurants, it’s situated on the levee near Frenchmen Street, overlooking the Mississippi.

Stay at the Frenchmen, a cluster of 1850s houses surrounding a courtyard with pool; some rooms have balconies (from £60).

New Orleans is 19.5 hours from Chicago by train (from £75); 15 hours (930 miles) by car; or just over 2 hours by plane (from £225).

Denver: From baseball games to old-school bars in the West
On the Road is driven by the allure of the West, and in particular Denver, Neal Cassady’s hometown and a Beat hub in the 1940s and ’50s. Kerouac came to the Colorado capital every time he travelled, lured by Denver ‘looming ahead of me like the Promised Land, way out there beneath the stars, across the prairie of Iowa and the plains of Nebraska’.

Built as a frontier mining town in the 19th century, Denver was booming in the ’40s. The characters from On the Road convene in the Windsor Hotel on Larimer Street, built during the Gold Rush and once Denver’s most luxurious lodgings. By the time the Beats made it their meeting place, it was a flophouse with bullet holes in the walls. The hotel was demolished in 1959.

The area has come full circle today. Larimer Street, the heart of skid row in On the Road, is now Lower Downtown, or LoDo, a hip area of restaurants, loft apartments and microbreweries created from century-old warehouses. The Great Divide Brewing Co is a first-rate example of new Denver, crafting excellent seasonal and year-round beers and selling them in its tap room.

On his second trip to Denver, Sal Paradise watches a game of softball played under floodlights on Welton Street, a ‘great eager crowd’ roaring at every play. These days, equally excitable crowds gather a few blocks away at gleaming Coors Field, home to the Colorado Rockies baseball team. Games cost from £38, or tour the stadium for £4.50.

Original Beatnik haunts do survive in the city. Kerouac used to visit the tiny, timeless El Chapultepec, a no-thrills jazz legend with red chequered floors and a stage that’s hosted Frank Sinatra and Ella Fitzgerald. Local jazz bands now take the stage nightly. Armed with a great old neon sign and beaten-up vinyl booths, Don’s Club Tavern is another relic of the Beats’ time, an old-school dive bar that opened in 1947, and was allegedly another of Kerouac’s drinking holes.

Before leaving town on the last leg of your trip, it’s worth checking out the ’50s-era signs scattered along Colfax Ave. Stretching east as US 40, it’s one of the country’s earliest cross-country routes. Sal and his Beat mates spend a lot of time on this road, living in an apartment there and drinking in its bars. When Dean Moriarty finally leaves Denver, he does so by roaring ‘east along Colfax and out to the Kansas plains’.

The Brown Palace is one of America’s great historic hotels. It opened in 1892 after its owner had been refused entry to the Windsor Hotel because of his cowboy get-up (from £160).

Denver is 19 hours by train from New Orleans (from £160); 22 hours (1,370 miles) by car; or a 3-hour flight (from £75).

San Francisco: Books, Beat and rolling fogs at the end of America
No city in America holds on to its past or regards anything resembling a national chain with as much suspicion as does San Francisco, or ‘Frisco’ as Kerouac dared to call it (locals hate the monicker). It’s a city of the individual, of rebels and romantics, and where inhibitions are frowned upon.

This spirit emerged in the same period that the Beats settled in, along with poets and artists, followed a couple of decades later by hippies and gay-rights activists. After WWII, when soldiers returning from the Pacific boosted the population, the city looked much as it does now. There are still 1940s-era streetcars running along Market Street and the fog still comes ‘streaming though Golden Gate to shroud the romantic city in white’ as it did in On the Road.

Sal arrives in San Francisco for his second visit after a wild cross-country ride with Dean, who yells, ‘“We can’t go any further ’cause there ain’t no more land.”’ The Beats’ activity in the city centered around North Beach, an Italian neighbourhood just north of Chinatown. The area is watched over by Art Deco Coit Tower on Telegraph Hill – take the lift to the top for panoramic views over the whole bay and the ‘eleven teeming hills’ that surround it.

The Beat Museum is a short stroll south. At this shrine to all things Beat Generation, you can see old film footage about the era’s leading writers, artists and musicians, trawl through first editions of Beat literature, and perhaps pick up a Kerouac bobble-head doll for your dashboard. Further south, Jack Kerouac Alley is a shortcut between North Beach and Chinatown, and a monument to the writer. Look out for the inscription from On the Road: ‘The air was soft, the stars so fine, the promise of every cobbled alley so great.’

The alley leads to City Lights bookstore, opened in 1953 by poet and publisher Lawrence Ferlinghetti. Poetic justice has been served here since 1957, when Ferlinghetti won a landmark freespeech ruling when he was pulled up on an obscenity charge for publishing Allen Ginsberg’s incendiary Howl. Head upstairs to the Beat section if you want a copy of it, or of the original scroll version of On the Road.

Nearby Vesuvio Cafe is a Beat-era remnant, with Tiffany lamps and old photos. Kerouac once skipped a meeting with author Henry Miller to drink himself silly here – though not with the tequila, rum and OJ cocktail now dubbed the ‘Kerouac’.

Before leaving town, Sal fulfils his own promise to climb ‘that mountain’. On a beautiful day, surrounded by California cottonwood trees, he looks over the Pacific, back to the city where he imagines ‘beautiful women standing in white doorways’, then east towards the ‘great raw bulge and bulk of my American continent’. That mountain, north of the city, is Mount Tamalpais. Find your own Sal Paradise moment on Mount Tamalpais State Park’s 50 miles of hiking and biking trails, which include a half-mile trip up East Peak. Perhaps at the top, ‘at the end of America’, you’ll find, like Sal, that there’s ‘nowhere to go but back’.

Boutique Hotel Bohème, in North Beach, looks to the Beats for its inspiration, with retro fabrics and ’50s photos (from £125).

San Francisco is 34 hours from Denver by train (from £100); 20 hours (1,300 miles) by car; or a 2.5-hour flight (from £70).

The article 'Jack Kerouac’s US road trip' was published in partnership with Lonely Planet Traveller.