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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’.

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