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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.

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