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0 Layers

Kerouac's "On the Road" Trip

Nothing behind me, everything ahead of me, as is ever so on the road.

  • 12
  • 61:54
  • $435
  • 4,092 mi.
Take This Trip

Created by Roadtrippers - April 18th 2017

There's no better case for a good road trip than Jack Kerouac's iconic novel "On the Road". Based on his journeys crisscrossing the country with other famous beatniks like Allen Ginsberg and Neal Cassaday as they sought to find America, visions, freedom, love, happiness, and, in a lot of ways, the meaning of life. Kerouac says that "The best teacher is experience and not through someone's distorted point of view", so experience his journey of self-discovery for, well, yourself with this trip.

Jack Kerouac's House

454 West 20th Street, New York, NY, US

Jack Kerouac's House

This 1850s brownstone is where Kerouac composed his legendary On the Road in a single six-week outpouring of exceptional creation.

0mi 00h 05m
Village Vanguard

178 7th Ave S, New York, NY, US

Village Vanguard


The Village Vanguard is a classic Greenwich Village beatnik establishment. Kerouac performed jazz poetry here in the 1960s.

0mi 00h 03m
White Horse Tavern

567 Hudson St, New York, NY, US

White Horse Tavern


Another bohemian favorite, the White Horse Tavern started gaining notoriety in the literature scene when Dylan Thomas drank himself to death here in 1953. Kerouac and Ginsberg hung out together here, and Hunter S. Thompson was also a regular. Pro tip: over the urinals in the men's room, you'll likely find graffiti that reads "Jack, go home!" which is a tribute to the fact that Kerouac was drunkenly thrown out of here more than a few times. The original writing is gone, but people keep writing it there!

801mi 12h 14m
Green Mill Jazz Club

4802 N. Broadway Ave, Chicago, IL, US

Green Mill Jazz Club


Kerouac spent some time in Chicago, so while you're in town, head to one of the few jazz bars from his day that's still kickin', the Green Mill. A favorite of Al Capone and Frank Sinatra, they still feature live jazz, swing, and big band music, and even host a slam poetry night once a week.

1012mi 14h 37m
Don's Club Tavern

723 E 6th Ave, Denver, CO, US

Don's Club Tavern


Kerouac's main character found himself in Denver a few times throughout the course of the book, and it's almost certain that Kerouac himself enjoyed a drink or two at Don's Club Tavern when he visited himself. It's a pretty classic dive bar, no frills... just the kind of place you'd wanna go while looking for the real America.

2mi 00h 13m

1962 Market St, Denver, CO, US



Kerouac used to visit the tiny, timeless El Chapultepec, a no-thrills jazz staple with red checkered floors and a stage that has hosted Frank Sinatra and Ella Fitzgerald. Local jazz bands now take the stage nightly.

1267mi 17h 41m
City Lights Bookstore

261 Columbus Ave, San Francisco, CA, US

City Lights Bookstore


Beat poet Lawrence Ferlinghetti and Peter D. Martin founded City Lights Bookstore, a shop and indie publishing house that has been a favorite of San Francisco residents for generations. Ferlinghetti won an important court case here, arguing that Ginsberg's poem "Howl" was free speech. The top floor is entirely dedicated to beatnik authors, so poke around and grab a copy of a Kerouac classic.

0mi 00h 00m
Vesuvio Cafe

255 Columbus Ave, San Francisco, CA, US

Vesuvio Cafe

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This European-style coffee house and bar was a favorite hangout of Kerouac and his crew... it's across the street from City Lights. Neal Cassady, the real-life Dean Moriarty put this place on the map when he stopped here before a poetry reading, and Kerouac was known to spend many a long night drinking here.

0mi 00h 01m
Jack Kerouac Alley

formerly Adler Alley, San Francisco, CA, US

Jack Kerouac Alley


The alley that connects City Lights and Vesuvio was renamed for Jack Kerouac. The street sign makes for a pretty great photo op.

0mi 00h 01m
The Beat Museum

540 Broadway at Columbus Ave, San Francisco, CA, US

The Beat Museum

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The Beat Museum is a veritable shrine to the beatnik generation. Located in North Beach, the neighborhood frequented by beats like Kerouac, Cassaday, Ginsberg, and more, it contains original manuscripts and first editions, letters, personal effects and cultural ephemera from famous and world-changing writers.

0mi 00h 01m
Hotel Boheme

444 Columbus Ave, San Francisco, CA, US

Hotel Boheme


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great deal for this hotel


Near the Beat Museum is the perfect hotel for Kerouac-inspired weary travelers. Hotel Boheme is reasonably priced and oozes beatnik vibes. Gauze-draped canopies over the beds, colorful paint, parasols, and photos of jazz greats decorate the hotel. Enjoy sherry in the lobby and cozy up with a book in your room!

1005mi 16h 58m

North Cascades National Park, Sedro-Woolley, WA, US

Desolation Peak Trail

End your adventure on the road with a trip to the North Cascades. Hitch a boat ride across Ross Lake and hike Desolation Peak Trail to the fire lookout atop the mountain where Kerouac spent 63 days during the summer of 1956, with little to do but eat, sleep, read, and write. The building remains a popular mecca for Kerouac-inspired pilgrimages, and you can spend a night here looking out at the view about which he wrote so fondly. You might even meet others seeking Kerouac's wisdom and inspiration along the way.


The best of Roadtrippers - hand picked by our team!