City Lights, Kerouac & North Beach Beats: A Literary Adventure

San Francisco, CA

  • Washington Square Park by David Ohmer - Flickr (CC BY 2.0)
  • Benjamin Franklin Memorial - Washington Square
  • Columbus Avenue - Transamerica Building by Russ Caldwell
  • Columbus Avenue on the map today -
  • Caffe Trieste - Vallejo & Grant
  • Caffe Trieste by Mobilus In Mobili / Flickr (CC BY 2.0)
  • The jazz mural in 1987-1988, when it was first painted. (Photo: Bill Weber)
  • The Beat Museum -- all about Jack
  • "Sin & Salvation" at Columbus & Broadway by Russ Caldwell
  • Language of the Birds after dark - Brian Goggin
  • Words falling on the pavement below - Brian Goggin
  • City Lights, Kerouac & North Beach Beats: A Literary Tour by Sherri Caldwell
  • Sherri's  Pilgrimage to City Lights Books by Russ Caldwell
  • Jack Kerouac Alley - Follow the street sign by Sherri Caldwell
  • Jack Kerouac Alley - San Francisco by Sherri Caldwell
  • Vesuvio Cafe by Day by Sherri Caldwell
  • Vesuvio at Night by Scott Swigart / Flickr (CC BY-SA 2.0)

2 hours
0.5 mi
Guided by The Rebel Housewife


In 1953, Lawrence Ferlinghetti co-founded City Lights Pocket Books in the heart of San Francisco's North Beach community. The tiny, triangle-shaped bookstore quickly became a bat-signal for the literary counterculture of the Beat Generation: Jack Kerouac drifting in *On The Road*, Allen Ginsberg HOWL(ing), Neal Cassady and friends shamelessly carousing through the artsy cafes, funky bars, notorious strip clubs and adult establishments nearby.

About Your Guide

Hi, I'm Sherri-- GenX author and journalist, a West Coast Girl transplanted to Atlanta, GA to raise a family... where I started writing women's humor as The Rebel Housewife(tm). As an avid reader, author fangirl, teacher, and literature & history geek in general, I love to research, travel, and explore the world by the book, so to speak... Wherever you go, there are spellbinding true stories just below the surface of time and current scenery, beyond the pages of a travel guide-- the history, scandals, drama and gossip, tragedies, crimes and mysteries... spooky ghost stories, too! I specialize in Books & Travel - Literary Adventures - connecting readers to a destination through the great books, famous authors, and fascinating stories of a particular location, city, or country. Enjoy!

Go on this Sidewalk

Guide Points

  1. Washington Square Park

    *Today, Washington Square is the heart of North Beach, as it has been for many years. Italian and Chinese residents mix with tourists and t…

  2. Columbus Avenue - North Beach

    Columbus Avenue cuts an infamous path through Little Italy and Chinatown. From its start at the base of the Transamerica Pyramid to its ter…

  3. Caffe Trieste

    Whether it’s early morning or late night, you’ve got to stop by Caffe Trieste, at least once, for the ambiance, history, and incredible Ita…

  4. Jazz Mural

    This intersection is a touchstone and gateway to the very heart of the Beat Generation in San Francisco: This. Is. It!

  5. The Beat Museum

    Museum. Bookstore. Curiosity Shop.

  6. Language of the Birds

    What earlier might have looked like styrofoam take-out containers suspended on the wires above, after dark becomes an amazing light show— t…

  7. City Lights Books

    City Lights is a landmark independent bookstore and publisher that specializes in world literature, the arts, and progressive politics.

  8. Jack Kerouac Alley

    Normally, you might worry about stepping outside at midnight into an alley, thinking of the dark, dingy, possibly dangerous sidestreet alle…

  9. Vesuvio Cafe

    *Vesuvio has never been just a bar. It’s true that booze sales pay the bills, but the place is also an art gallery, a museum, a living room…

About Sidewalk

Sidewalk is an app that provides free, guided walk experiences that can be created by anyone with stories to share about places they know and love.

The app navigates people through a neighborhood walk using GPS turn-by-turn directions, rich imagery and storytelling.