Walking San Francisco

The rainbow flag, designed by activist Gilbert Baker, first flew at the Gay Freedom Day Parade in 1978; today, it remains a vibrant emblem of gay pride.

PARKING: You might try your luck along Guerrero or Valencia St. Off-street parking is available at the Market and Noe Garage.

The Castro District, or the Castro for short, proudly celebrates its distinction as one of the first and most recognized gay meccas in the United States. But in addition to being at the forefront of civil rights as it pertains to marriage equality and gay, lesbian, bisexual, and transgender inclusion, it is also a treasure trove of lovingly maintained architectural gems, with unbroken strings of beautiful Victorian houses along many blocks.

An enclave of Eureka Valley, the Castro was known in the early 1900s as Little Scandinavia for the all the working-class immigrants from Norway, Sweden, Denmark, and Finland who settled here, bringing dairy farms and half-timbered architecture. During World War II, the military dismissed thousands of gay servicemen from the Pacific, and they found themselves landing in San Francisco’s port.

The Polk Street area (see Walk 13, Tenderloin) was the city’s original “gayborhood,” but couples began drifting inland toward Castro Street in the early 1970s. They were most likely drawn by the well-priced Victorian houses and the winning location, with streets terracing up the eastern slope of Twin Peaks (see next walk), which on most days shields the Castro from the fog. The neighborhood’s quiet residential streets reflect the refined tastes of its denizens, who are by and large established professionals.

Castro Street between Market and 18th Streets is the busy commercial hub, with Upper Market taking on much of the spillover. This tour will take in both sides of the district: the elegant homes as well as the bars and clubs that reflect the Castro’s flamboyant social side. (The Twin Peaks walk explores the western part of the neighborhood, which climbs the western slopes of the prominent hills.)

Walk Description

We’ll begin our tour well east of Castro Street, at the corner of Market and Octavia Streets. Here, at 1800 Market, the vivid purple

SF LGBT Center stands as a welcoming portal to the neighborhood, with rainbow flags flapping proudly from each window. It offers services and programs for lesbians, gays, bisexuals, and trans people, including career counseling, youth mentorship, and healthcare resources. The center is architecturally interesting, as it consists of a historic Victorian that segues into a strikingly modern wing of tinted glass panels that meet at oblique angles. It’s a suitable introduction to the neighborhood, where appreciating the old doesn’t preclude embracing the new.

Heading west on Market Street, a few blocks up, on the same side of the street, you come to the

Mint Karaoke Lounge, a little neighborhood dive that gets its name from the nearby U.S. Mint, which can be seen soon after you pass the bar. The Mint is a popular nightclub that draws a fairly mixed crowd, though it appeals mostly to hammy would-be singers eager for their turn at the mic. The U.S. Mint, up on the hill, is a foreboding structure that looks more like a futuristic military installation than a place that produced money. It no longer creates currency, but it does still churn out commemorative coins that are highly collectible.

Slide into Cafe du Nord for local musical acts and an old-school cocktail lounge vibe.

Up Market Street a couple of blocks west, just before the corner of Sanchez Street, is

Cafe du Nord. The name is French, the architecture is Scandinavian, and the classy below-street-level joint is pure swank with a hip, modern edge. The onetime speakeasy is a mainstay on San Francisco’s small-venue live-music scene, with a regular lineup of independent acts, many local and mostly worth catching. Upstairs, the Swedish American Hall is no meatball parlor but another excellent live-music venue. It has the look and feel of a Masonic lodge, with heavy Alpine woodwork. Events are scheduled here infrequently, though.

Across Market Street, at the corner of Noe Street,

Cafe Flore is a celebrated hangout where the patio tables are highly coveted on sunny days. As you can see, in construction it resembles a gardener’s shed, though on a much larger scale. Potted greenery contributes to the effect. But Cafe Flore is about coffee, beer, light meals, seeing, and being seen. A block up is

Catch, a well-regarded seafood restaurant and also an official city landmark, as it’s where the original AIDS Memorial Quilt was first conceived by activist Cleve Jones. Now considered the world’s largest community folk-art project, the quilt began as a way to honor those who died of AIDS but were denied funerals or recognition due to social stigma. You are welcome to enter the restaurant to see a small section of the quilt displayed just inside the front door.

The corner of Market and Castro Streets, where you turn left onto Castro, is naturally one of the principal crossroads of the neighborhood. A huge rainbow flag flaps in the wind from a pole high above

Harvey Milk Plaza, at the southwest corner. Named for the assassinated city supervisor, the cramped little plaza is tucked between a building and the entry to the Muni station, but its size did not prevent it from being a mobilizing point for countless civil rights rallies and some rather raucous dance parties. It was here that Harvey Milk stood on an overturned box with a bullhorn to motivate support, and it was here that tens of thousands gathered in the wake of Milk’s death for a spontaneous candlelit march to City Hall in 1978. The vigil is repeated every year.

Twin Peaks Tavern earned landmark status for being the first Castro watering hole with clear glass windows, doing away with the shame and secrecy of being seen in a gay bar.

Just beyond the rainbow flag, wedged on the busy intersection between 17th Street and Market, is

Pink Triangle Park, the nation’s only memorial to gay and lesbian servicepeople who were killed in World War II. The memorial comprises 15 stone columns, each representing 1,000 fallen soldiers and each topped with a pink triangle—the symbol that the Nazis forced gay and lesbian concentration-camp inmates to wear on their uniforms.

On the opposite side of Castro Street, across from Harvey Milk Plaza,

Twin Peaks Tavern attracts an older crowd of regulars. The bar has historic charm but has come a long way from its 1935 blue-collar roots. The neighborhood’s biggest landmark is the

Castro Theatre, a few doors up Castro Street from the Twin Peaks Tavern. There aren’t many movie palaces of this sort left anywhere in the country, which is why the Castro is treasured by all San Franciscans. The programming is eclectic, featuring a mix of independent films, bawdy sing-alongs, and screenings of camp classics such as Mommie Dearest and Valley of the Dolls, as well as pristine prints of iconic movies. The show is often preceded by an artful performance on the house organ, and on occasion the Castro screens silent films with a live pit orchestra. Several film festivals take place here as well. The building, a Moorish flight of fancy, is particularly dramatic at night, when the marquee is lit up. It was built in 1922, and the plans were drawn by architect Timothy Pflueger.

A couple of doors farther along,

Cliff’s Variety is the neighborhood hardware store, although that moniker hardly does it justice. In business since 1936, the Asten family that ran Cliff’s was open to the changing neighborhood and was one of the first straight-owned stores to hire gay employees. Along with the usual plumbing and electrical fixtures, you can also stock up on feather boas, diamond tiaras, games, and housewares. On the same block,

Dog Eared Books is an independent bookstore that hosts an LGBT book club and a regular series called Perfectly Queer Reading; they also specialize in small-press books and local publications.

The bookshop is just a few paces from the rainbow crosswalk corner of Castro and 18th Streets, which is considered the nexus of the neighborhood. There are restaurants and hangouts in either direction along 18th Street; turn right and walk half a block to reach the

GLBT History Museum, one of few of its kind in the world. The museum is tiny, but $5 gains you access to a variety of audio recordings, photos, and historical information. It’s closed on Tuesdays.

Retrace your steps to continue up Castro. At No. 575, Harvey Milk ran Castro Camera during the 1970s; today it’s the

Human Rights Campaign Store. A bronze plaque on the sidewalk commemorates Milk’s contributions to the local community, and you can see a painted Harvey smiling down from the window of the upstairs unit where he once lived. The

Anchor Oyster Bar next door, family owned since 1977, is a local favorite for fresh seafood dishes. The cioppino (seafood stew) is highly recommended.

Just past 19th Street, Castro Street turns residential, with an impressive row of Victorian apartment buildings stacking up along the incline. Turn left on Liberty Street, which looks much as it would have more than a century ago. Immaculate single-family homes, nearly uniform in character, line both sides. These were middle-class homes originally but are worth six and seven figures today. From here, you could continue down Liberty Street (there’s a staircase) and head toward Dolores Park and the Mission, or you can return to the Castro and window-shop along 18th Street.