Stranger than Fiction: A Literary Walking Tour of SF

SF Beat Museum

Since the early days of the Gold Rush, San Francisco's given rise to an impressive cast of authors, poets, and literary game-changers. Some were born here; many made conscious decisions to relocate to the famously freethinking city; others simply took a liking to the place while passing through. But regardless of where they came from or how long they stayed, they all left their marks on the city in one way or another. 

Some, though, left the kind of marks you can actually see today. For this edition of Stranger than Fiction, we're showing you how to pay homage to writers from Robert Louis Stevenson to Mark Twain, Jack Kerouac to Dave Eggers, in the here and now. 

"The city of San Francisco, and the bay of gold and corn were lit from end to end with summer daylight."– Robert Louis Stevenson

Robert Louis Stevenson plaqueStart your tour off on Bush Street near Stockton Street, about a 10-minute walk from HI-SF Downtown or a 20-minute walk from HI-SF City Center. At 608 Bush Street, wedged in between a laundromat and a barbershop, you'll notice a building with an arched entryway flanked by glass lamps. The aesthetic flourishes might seem a bit out of place given the building's rather unglamorous surroundings, but look a little closer and you'll see the area's actually got a rather distinguished history: a plaque mounted at one side of the archway notes that Robert Louis Stevenson lived on this site from 1879-1880. The Scottish author of Treasure Island and The Strange Case of Dr. Jekyll and Mr. Hyde spent about a year in San Francisco while, quite scandalously, waiting for the married American with whom he'd fallen in love to divorce her husband. 

From 608 Bush Street, continue down Bush towards Grant, then make a left on Kearny Street. Follow Kearny a few blocks down to Clay Street, where you'll arrive at Portsmouth Square Plaza.

Stevenson was a consummate traveler and spent only a year in the City by the Bay before moving on, though he certainly entrenched himself in the local life while he was here. He wrote often during his time in the city, became a great fan of Emperor Norton, and made frequent visits to Portsmouth Square in the heart Chinatown. Often referred to as "Chinatown's living room," the square is today a gathering place for that neighborhood's residents: every day of the week you'll find old men on benches playing card and board games, and groups of people practicing a spiritual and physical exercise known as Falun Gong. You'll also find a large monument to Stevenson: a tall stone pillar topped, appropriately, with a ship, its sails full of wind.  

From Portsmouth Square Plaza, walk down Merchant Street for about two minutes until you reach Montgomery Street.

"I have always been rather better treated in San Francisco than I deserved." – Mark Twain

Transamerica PyramidAt the corner of Montgomery and Merchant Streets, you'll find one of San Francisco's most famous buildings: the iconic Transamerica Pyramid. Today, the pointy tower's a prominent feature in the city's skyline, but there was a time when an even more famous building stood on the site the pyramid occupies today. Built during California's Gold Rush days, the Montgomery Block building was the state's first earthquake- and fire-proof structure (a quality that would serve the building well during the city's devastating 1906 earthquake and fire). Once the largest building west of the Mississippi, the Montgomery Block provided office and living space for countless lawyers, artists, and writers until its demolition in 1959. Writers who lived, worked, or visited here over the years include Stevenson, Ambrose Bierce, Jack London, and Mark Twain.

The Montgomery Block looms particularly large in Twain's legend: it was in the building's basement sauna that Twain met a local firefighter named Tom Sawyer, taking a liking to the name and filing it away for future use. 

Though the Montgomery Block building is long gone, a plaque inside the Transamerica Pyramid's lobby commemorates the literary importance of the site. Just off to the side of the pyramid, a Privately Owned Public Open Space filled with redwood trees offers a forested escape in the middle of the city's bustling Financial District. Inside the little park, a fountain ringed with leaping bronze frogs is a whimsical nod to Twain, whose first taste of fame came with the publication of his story "The Celebrated Jumping Frog of Calaveras County." 

Mark Twain Frog FountainKeep your eyes close to the ground and you may notice a plaque commemorating two other famous San Franciscans: Bummer and Lazarus, a pair of stray dogs who captured the heart of the city in the 1860s. If you find yourself wondering how popular a couple of mutts could be, consider this: when Bummer died in 1865, Mark Twain wrote his obituary for a local newspaper.

From the Transamerica Pyramid, walk about five minutes down Columbus Ave., approaching Broadway.

"The light of San Francisco is a sea light, an island light, and the light of fog blanketing the hills drifting in at night through the Golden Gate to lie on the city at dawn." – Lawrence Ferlinghetti

City Lights BooksClustered together right around the intersection of Columbus and Broadway, you'll find a trio of testaments to San Francisco's more recent literary history. Make your way into City Lights Bookstore, arguably one of the most famous bookstores in the country, for a quick immersion into the Beat era of Jack Kerouac, Allen Ginsberg, and Lawrence Ferlinghetti

Ferlinghetti, author of one of the most popular books of poetry of all time (A Coney Island of the Mind), founded City Lights in 1953. What started out as the nation's first all-paperback bookstore has evolved over the years into much more: today, City Lights is a treasure trove of hard-to-find titles, translations from around the world, politically progressive literature, and the kind of novels that were once banned in classrooms. It's also a publishing house that puts out works of poetry, fiction, non-fiction, and more. City Lights gained notoriety in 1957 when Ferlinghetti was tried for obscenity after publishing Allen Ginsberg's seminal Howl and Other Poems; when the court ruled in Ferlinghetti's favor, it opened the door for the American publication of Henry Miller's Tropic of Cancer, D.H. Lawrence's Lady Chatterly's Lover, and other books once deemed too inappropriate for release in America.

Kerouac Alley pavement stoneRight next to City Lights you'll find a colorful alley dedicated to Ferlinghetti's buddy Jack Kerouac. Christened Jack Kerouac Alley and opened to the public in 2007, the narrow passageway is hemmed in by colorful murals, and its brick pathway is quite literally lined with poetry: quotes from the likes of Kerouac, Ferlinghetti, and Maya Angelou are inscribed on large stones that pave the walkway.



Vesuvio CaffeJust across the alleyway from City Lights, Vesuvio Café is another remnant of the area's Beat past. The bar was once a regular hangout for Kerouac and his contemporaries; today it's still a favorite of locals and tourists alike. Grab a table, order up a "Bohemian Coffee" spiked with brandy and Amaretto, thumb through your dog-eared copy of On the Road or Big Sur, and you'll fit right in.



On the Road Car SF Beat MuseumOn Broadway, almost kitty-corner from City Lights, a huge black-and-white painting of Kerouac and his friend (and inspiration) Neal Cassady pulls passersby into the Beat Museum. Part store, part shrine, this place has been carrying on the progressive spirit of the Beat generation since 2003: this is the spot to score hard-to-find titles by not just Kerouac and Ginsberg but also the likes of Hunter S. Thompson, Charles Bukowski, and William S. Burroughs. It's also the permanent home of the 1949 Hudson that Sam Riley and Garrett Hedlund, as Sal Paradise and Dean Moriarty, drove cross-country in the 2012 big-screen adaptation of On the Road.

The store portion of the Beat Museum is free to browse, and for $8 ($5 for students), you can gain entry to the museum itself. Inside you'll find a huge collection of memorabilia, original manuscripts and first editions, personal letters, and more from prominent figures of the Beat era.  

"But of course there's no logic to San Francisco generally… It's the work of fairies, elves, happy children with new crayons." – Dave Eggers


Pirate StoreThough so many important literary sites are clustered tightly (and conveniently) in San Francisco's downtown area, there are several others worth a trek to further-flung parts of the city. On a wall of what's now the Wells Fargo Bank building at 490 Brannan Street (near 3rd Street), a plaque marks the birthplace of Jack London, author of White Fang and The Call of the Wild. 

Fans of more contemporary literature won't want to leave San Francisco without making a stop at 826 Valencia Street in the Mission District. Dave Eggers, the wildly popular author of A Heartbreaking Work of Staggering Genius, lives in Northern California and set up his 826 Valencia foundation in the Mission in 2002. The nonprofit foundation offers tutoring to local schoolchildren and has been expanded to half a dozen other cities across the country. To help fund its programming, the organization has set up a full-service "Pirate Store" at its eponymous address. What exactly does a pirate store sell? Consider this notice posted at the front of the shop: "If you can find a wider selection of higher-quality eye patches for more occasions in the Mission, we'll personally find and replace your missing eye free of charge." 

"No city invites the heart to come to life as San Francisco does. Arrival in San Francisco is an experience in living." – William Saroyan

San Francisco may be a city of writers and stories like no other, but remember: the greatest San Francisco adventure is your own. So take a cue from Twain, Kerouac, and the rest, and get out there and live it! 


If You Go 

Stay at one of our three San Francisco hostels, and check out a map of all the sites mentioned in this story.