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.
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!
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.
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.
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.
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.
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.
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!
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.