The USA is a big country, and whenever anyone’s tried to define it – be they a Charles Dickens, a Mark Twain or a Stephen Fry – they’ve hit the road. So did the Beat Generation in the 1940s. 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. 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 Coloradan who marks his trips with a 'wild yea-saying overburst of American joy.'

Can you travel the road in that same spirit today? Well, 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 four 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 City

New York is the city that never sleeps – and it was particularly awake after WWII. 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. It was in Harlem jazz joints that fast-tempo bebop developed out of old-school jazz, and ‘bop’ soon became the soundtrack for the Beats. 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. 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.

When not at his desk, Kerouac hung out with Allen Ginsberg at the 19th-century White Horse Tavern, made infamous as the site of Dylan Thomas’s fatal drinking binge in 1953. The pub has since 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. Sal sits on an ‘old broken-down pier’ on the Hudson River and watches the sun set. 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.'

Cyclists and strollers head over the Brooklyn Bridge. Photo by Kris Davidson.


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 divide their time between the historic Loop district and Uptown. 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 is now home to Chicago’s financial district as well as museums, galleries and Millennium Park with free summer concerts.

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 the following morning. 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. A trapdoor behind the bar leads to tunnels where they hid their bootlegged booze. Today, jazz is played nightly – afterwards, stagger out ‘into the great roar of Chicago... to sleep until the wild bop night again’.

The Chicago skyline at dusk as seen from Northerly Island. Photo by Kris Davidson.


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. 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.

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.

Original Beatnik haunts do survive in the city. Kerouac used to visit the tiny, timeless El Chapultepec, a no-frills 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. When Dean Moriarty finally leaves Denver, he does so by roaring 'east along Colfax and out to the Kansas plains'.

Highway leading travellers out of Denver. Photo by Kris Davidson.

San Francisco

No city in America holds on to its past or regards anything resembling a national chain with as much suspicion as does San Francisco. 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.

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 centred 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 Language of the Birds, a mural in North Beach features a flock of 23 books and words from local authors. Photo by Kris Davidson.

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, and pick up a Kerouac bobble-head doll for your dashboard. Nearby Jack Kerouac Alley leads to City Lights Bookstore, opened in 1953 by poet and publisher Lawrence Ferlinghetti, who was famously 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. Steps away, 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.

Before leaving town, Sal fulfils his own promise to climb 'that mountain'. That mountain, north of the city, is Mt Tamalpais. On a beautiful day, he looks over the Pacific, back to the city, then east towards the 'great raw bulge and bulk of my American continent.' Find your own Sal Paradise moment on the park’s 50 miles of hiking and biking trails. Perhaps at the top, 'at the end of America,' you’ll find, like Sal, that there’s ‘nowhere to go but back'.

This is an excerpt from a longer feature by Robert Reid, first published in Lonely Planet Traveller magazine.

Robert Reid is Lonely Planet's US Travel Editor.

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