Featured Trips Types:

  • All Featured Trips
  • 48 Hour City Guides
  • Camping & Road Trips
  • Family Road Trips
  • Ghost Guides
  • Weird Guides
  • National Parks Trips & Tips
  • Outdoor Escapes
  • Classic USA Road Trips
  • Interstate Highway Exit Guides
  • Scenic Drives
  • Airstream - Live Riveted
  • Thor Industries
  • Fun for the Whole Family
  • Grand County
  • Explore Memphis like a Local
  • Offbeat Camping
  • Scenic Routes
  • Outdoor Adventure
Clear All

Accommodation Types:

  • All Accommodation
  • Bed and Breakfasts & Inns
  • Boutique Hotels
  • Hostels
  • Hotels
  • Motels
  • Unique Stays


Look for FastBook for quick links to
your favorite booking sites

Clear All

Attractions & Culture Types:

  • All Attractions & Culture
  • Amusement Parks
  • Children's Attractions
  • Fall Attractions
  • Museums
  • Offbeat Attractions
  • Top Attractions
  • Tours & Excursions
  • Winter Attractions
  • Zoos & Aquariums
Look for the icon to book the best
tours and activities nearby.
Clear All

Food & Drink Types:

  • All Food & Drink
  • Bars & Drinks
  • Burgers & BBQ
  • Coffee & Tea
  • Delis & Bakeries
  • Diners & Breakfast Spots
  • Ice Cream & Sweets
  • Restaurants
  • Vegetarian & Health Food
  • Wineries, Breweries & Distilleries
Clear All

Outdoors & Recreation Types:

  • All Outdoors & Recreation
  • Beaches
  • Fall Foliage
  • Geographical Areas
  • Geographical Features
  • National Parks
  • Nature Reserves
  • Parks & Gardens
  • Scenic Point
  • Swimming Spots
  • Trails & Hikes
Clear All

Points of Interest Types:

  • All Points of Interest
  • Abandoned
  • Architecture
  • College Icons
  • Film & TV
  • Historic
  • Holiday Lights
  • Literature
  • Military
  • Monuments
  • Photo Op
  • Planes, Trains, Autos
  • Public Art
  • Science & Tech
  • Spooky Places
Clear All

Vacation Rentals Types:

  • All Vacation Rentals
  • HomeAway
  • Vacation Rentals

We’ve partnered with HomeAway to find you the perfect vacation rental.

Clear All

Camping & RV Types:

  • All Camping & RV
  • Cottages & Cabins
  • KOA Campgrounds
  • RV Parks
  • Tent Campgrounds
Clear All

Entertainment & Nightlife Types:

  • All Entertainment & Nightlife
  • Art Galleries
  • Casinos & Gaming
  • Cinemas
  • Games & Amusements
  • Music
  • Nightlife
  • Shows & Entertainment
  • Theaters
Clear All

Services Types:

  • All Services
  • ATMs
  • Auto Services
  • Gas/Fuel Stations
  • Rest Areas
  • Tourist Information
  • Transportation
  • Vehicle Rental
Clear All

Shopping Types:

  • All Shopping
  • Antiques
  • Books & Music
  • Crafts & Handmade
  • General Goods
  • Gifts & Souvenirs
  • Groceries
  • Malls & Shopping Areas
  • Quirky Shops
  • Thrift & Flea
Clear All

Sports Types:

  • All Sports
  • Adventure Sports
  • Cycling
  • Equestrian Sports
  • Fishing & Hunting
  • Golf
  • Gyms & Fitness
  • Skate & Surf Spots
  • Stadiums
  • Water Sports
  • Winter Sports
Clear All

Motoring Types:

  • All Motoring
  • Automotive Attractions
  • Off-Road Trails
  • Racetracks
  • Scenic Drives
Clear All
  • Trip
  • Places I've Been
  • My Saved Places
  • Collection
  • Featured Trips
  • Accommodation
  • Attractions & Culture
  • Food & Drink
  • Outdoors & Recreation
  • Points of Interest
  • Vacation Rentals
  • Camping & RV
  • Entertainment & Nightlife
  • Services
  • Shopping
  • Sports
  • Motoring

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
  • 4,092 mi
  • $435
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

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

Village Vanguard

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


New York, NY

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!


Chicago, IL

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.

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.


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.


San Francisco, CA

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.


San Francisco, CA

Viator Find Tours

Click to find bookable tours and activities here

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.

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.


San Francisco, CA

Viator Find Tours

Click to find bookable tours and activities 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.


Click to find a
great deal for this hotel

Hotel Boheme

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!

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!