Today's the 56th anniversary of the release of Jack Kerouac's On The Road. The book chronicled the travels of "Sal" and "Dean," whose free-spirited adventures defined the postwar "beat" generation. Follow this On the Road-inspired route to hit up some of the major beatnik hotspots along Kerouac's iconic journey.
“I was surprised, as always, by how easy the act of leaving was, and how good it felt. The world was suddenly rich with possibility.”
Your first stop is Kerouac's house in New York City. This is where he wrote On The Road. Next up, visit the Village Vanguard (an essential beat stop), then head over to the 19th century White Horse Tavern and get properly smashed. This is where Dylan Thomas drank himself to death. Kerouac lived across the street. This was also a frequent haunt of Norman Mailer and Hunter S. Thompson
“Nothing behind me, everything ahead of me, as is ever so on the road.”
Next up, Chicago. Sal and Dean spent quite a bit of time in the historic Loop district of Chicago, which has undergone considerable changes since the mid-20th century. Now home to the financial district and Millennium Park. Though not mentioned in On The Road, if you're in Chi-Town, you've got to visit the Green Mill Cocktail Lounge. Poetry slams, coupled with 30s and 40s jazz, Kerouac would be proud.
“Our battered suitcases were piled on the sidewalk again; we had longer ways to go. But no matter, the road is life.”
Larimer Street was the heart of Denver's Skid Row, when Kerouac wrote On the Road. Now it's Lo-Do (Lower Downtown), a trendy area with loft apartments (cause loft apartments are totally trendy). You can still find some "beat" hotspots in the mile-high city. Throw back some drinks at the historic dive bar, Don's Club Tavern, where Kerouac got sloshed. Or try original Beatnik haunt, El Chapultepec. This is your standard "no-thrills jazz legend with red chequered floors." Kerouac, Sinatra and Ella Fitzgerald were all regulars. Today local jazz bands provide nightly entertainment.
"The air was soft, the stars so fine, the promise of every cobbled alley so great."
Your final stop is San Francisco. Stroll down Jack Kerouac Alley to City Lights Bookstore. When you visit this iconic beat generation bookstore, head upstairs to the Beat section to check out the scroll version of On the Road. Then walk in the footsteps of Neal Cassady (the real-life Dean Moriarty) and stop over at Vesuvio. The joint became a regular hangout for Kerouac and other Beat poets. Next, check out the Beat Museum, which is a shrine to the beatnik generation. You'll likely want to rest your weary head at Hotel Boheme, which oozes Beat-era jazz. Then end your journey as Sal did, atop breathtaking Mount Tamalpais.