Alleys as Anecdotes: A Tour of San Francisco's Most Fascinating Corners

San Francisco’s smallest streets tell the story of an ever-changing city.

The story of San Francisco is constantly evolving, but one element is static. To speak of San Francisco is to tell a tale of a city in flux, a community where churn and change and reinvention is the norm.

Aspects of San Francisco are charming here in a way that elsewhere they simply are not. Take our alleyways. Serving purposes as varied as shortcuts, commerce lanes, art spaces and restaurant rows, the alleys and narrow lanes of San Francisco showcase the character of the city, its history and present. While alleys serve as connective footpaths and thoroughfares, they also serve as bridges between the past and future. Within one city block, it’s easy to find remnants of the 1849 Gold Rush and the city’s storied literary legacy alongside contemporary art and technological innovation. And with many of San Francisco’s most interesting side streets, the most prominent features and figures make themselves known before one arrives.

Good Fortune

Chinatown is celebrated for its numerous alleys—41 total—that act as shortcuts for locals and eye candy for everyone else. Many date to the 19th-century era when San Francisco’s Barbary Coast lured gold miners seeking urban diversions when not striking it rich elsewhere. But Ross Alley, noted as the city’s oldest alley and famous for appearing in “Indiana Jones and the Temple of Doom,” may also be the most delicious alleyway destination in the historic neighborhood.

Golden Gate Fortune Cookie Factory

With lines frequently out the door, the Golden Gate Fortune Cookie Company is beloved for its samples and the up-close view of predictive advice being packaged in a tasty outer shell. Established in 1962, the humble shop is equal parts bakery and walking tour stop, with workers manning griddles and folding cookies by hand, and a sign noting a nominal fee to take photos with the diligent cookie masters.

Telling Tales

Russian Hill dwellers know exactly which narrow street beloved San Francisco novelist Armistead Maupin chose to depict as Barbary Lane in his contemporary classic, “Tales of the City.” Only two blocks long, leafy Macondray Lane tells another story: that of the impressive views from San Francisco’s steep hills. From this shady alley, one can absorb views of the San Francisco Bay all the way out to Alcatraz Island. Pleasantly residential Russian Hill feels a world away from the hubbub of nearby downtown, and a stroll down Macondray makes passersby feel so at home, many wish to move right in, too.

Maiden Lane

By Any Other Name

Another throwback to the Barbary Coast era, it’s difficult to imagine today’s tony Maiden Lane as a red-light destination during the Gold Rush. A shopping street now in stark contrast to its former purposes, the row is home to high-end retailers—some open by appointment only—and operates as a pedestrian-only passage during the day with strings of twinkling bulbs lighting the way each evening. But the most beloved fixtures are easily heard blocks away before they come into view. For two decades, professional opera singers Litz Plummer and Robert Close have offered their mellifluous tenor and soprano stylings for all to hear. Tips are encouraged.

Clarion Call

To wander down the brightly muraled Clarion Alley in the Mission District is to appreciate a signature San Francisco value: making use of any available space. Since 1992, the Clarion Alley Mural Project (CAMP) has used the 15-foot wide, 560 foot-long alley as a canvas for outrage and delight, depicting controversial figures and flowers in bloom. The alley’s oldest paintings date to 1994, though many pieces have evolved or been covered over the years, changing the same way the city often does. New folks come in and (hopefully) improve upon the legacy of those who came before.

Balmy Alley

The Mission is awash with art, as CAMP founders were inspired by nearby Balmy Alley, another bright side street where, since the 1970s, a similar community mural project has been underway. To see them both, meander through one of the city’s sunniest neighborhoods, an area equal parts residential and commercial, with taquerias and small shops nestled between doorways to walk-up apartments. Many parts of the Mission still look like the San Francisco of yesterday, and many others are evolving into what may be the San Francisco of the future.

One Thing Leads to Another

Trinity Place: Tucked into the heart of the Financial District, the Parisian-style cooperative bookstall and newsstand 34 Trinity Arts and News features periodicals; an array of rare and used books; and original prints; photos and zines by local artists.

Jack Kerouac Alley: Named for the iconic writer who chronicled the Beatnik scene, this short footpath borders City Lights, an independent bookstore also famed for its Beat poetry collection. Across the alley, Vesuvio Cafe features Beat writer memorabilia to accent strong, reasonably priced drinks.

Jack Kerouac Alley

Belden Place: A hub of activity for the city’s tiny French Quarter, Belden Place is a restaurant row featuring fine French cuisine (Plouf, Café Bastille) in addition to Italian bistro Café Tiramisu and seafood spot Sam’s Grill, a San Francisco institution since 1867.