DISTANCE: 2 miles (3km)
TIME: A half-day
START: Buena Vista Park
END: Castro and 16th streets
POINTS TO NOTE: This tour of the Castro begins at the entrance to Buena Vista Park at Haight Street and Central Avenue. To reach this starting point, take bus 6, 43, 66, or 71. This tour is a good one to do in the afternoon into evening, so consider doing it after walk 11.
The well-groomed Castro, considered by many to be the gay capital of the world, showcases beautifully restored Victorian and Edwardian homes, while draping its thriving nightlife, love of shopping, and political activism in rainbow flags.
LGBT-friendly district
iStockphoto
BUENA VISTA PARK
Dating from 1867, Buena Vista Park 1 [map] is San Francisco’s oldest park. When the city converted its many cemeteries into parks, workers were ordered to use the unclaimed headstones for the new trails and gutters. Out of respect for the dead, many decided to leave the pieces facing upwards; some of these are still visible today in Buena Vista Park.
Walk southwest along the steep sidewalk of Buena Vista Avenue West, which clings to the park’s edge, passing grand and beautifully restored Victorians. One of these, at No. 737, is the picturesque Spreckels Mansion 2 [map] (not to be confused with the mansion of the same name in Pacific Heights). Built in the late 19th century for sugarmagnate Richard Spreckels, the now private residence was also once home to Ambrose Bierce and Jack London.
Buena Vista Avenue West becomes Buena Vista Avenue East, turning sharply northeast. Take the path into the park here for breathtaking downtown views. Then continue on Buena Vista Avenue East, turning right on Buena Vista Terrace, left on 14th Street, and right on Castro Street, descending to Market Street and the colorful center of the Castro.
Castro Street
Dreamstime
THE CASTRO district
It was only 30 years ago that the Castro shifted from a working-class, Irish Catholic neighborhood to the city’s thriving, politically active gay hub, but it is hard now to imagine it any differently. San Francisco is often referred to as the gay capital of the world, a title its residents wear with pride. The active lesbian and gay community that has made its home in the Castro has contributed significantly to every area of San Francisco’s culture: economic, artistic, and political. Today, the tightly knit community is safe, well maintained, and filled with friendly eateries, unique shops, and brightly colored Victorians and Edwardians.
Harvey Milk Plaza
At the intersection of Castro and Market streets is Harvey Milk Plaza 3 [map]. Harvey Milk was a Castro Street camera shop owner and gay activist who organized the area’s merchants’ group. In 1977, he was elected to the Board of Supervisors, becoming the first openly gay city official to be elected in American politics. In 1978, former supervisor Dan White, the city’s most anti-gay politician, shot and killed Milk and Mayor George Moscone in their City Hall offices. The city reeled in shock, and a somber, mixed crowd marched from Castro Street to Ctiy Hall, silently bearing candles. Six months later, a jury sentenced White to just 5 years, with White avoiding a murder conviction with the infamous “Twinkie Defense,” which claimed a sugar high had reduced White’s mental capacity. The lenient sentence provoked enraged protestors to descend on City Hall in the White Night Riot of May 21, 1979, torching the capitol and police cars. White, paroled in 1985, committed suicide in the same year that The Life and Times of Harvey Milk won an Oscar for best documentary. In 2008, Sean Penn portrayed Harvey Milk in the biographical drama Milk.
Here also is historic Twin Peaks 4 [map] (401 Castro Street; www.twinpeakstavern.com; Mon–Wed noon–2am, Thur–Sun 8am–2am), a friendly neighborhood tavern and the country’s first openly gay bar.
Just to the west of this intersection, an island wedge between Market and 17th streets hosts the Pink Triangle Park and Memorial 5 [map] (http://pinktrianglepark.org). The 15,000 or so gays, lesbians, bisexuals, and transgenders who were persecuted during and following the Nazi regime are commemorated here by 15 white-granite pylons inlaid with pink triangles (the symbol once worn by LGBT concentration-camp prisoners) and positioned in the shape of a triangle.
Food and Drink
1 Samovar TEA LOUNGE
498 Sanchez Street; tel: 626-4700; www.samovarlife.com; daily 10am–10pm; $
Rest and recover while sipping small-batch artisan teas paired with international dishes. Private tea classes are also offered.
2 Café Flore
2298 Market Street; tel: 621-8579; www.cafeflore.com; daily B, L, and D; $
The diverse crowds that frequent this ever-bustling intersection make this café perfect for people-watching. Order your coffee, frittata, or club sandwich at the counter and pounce on a table on the sunny outdoor patio.
The Baroque façade of Castro Theatre
Nowitz Photography/Apa Publications
Castro Theatre
Castro Street, between 17th and 19th streets, is the neighborhood’s compact commercial center, packed with stores, bars, cafés, and restaurants. Head south on Castro Street for the Castro Theatre 6 [map] (No. 429; www.castrotheatre.com). This ornate yet intimate Spanish Baroque theater, complete with Art Deco flourishes, was built in 1922 and designated a U.S. National Landmark in 1977. The revival movie house new releases, independent films, musical sing-a-longs (Sound of Music, Grease, Mary Poppins), and film festivals, and on special nights a live organist plays on a platform that ascends before the start of the film.
Orphan Andy’s 24-hour restaurant
Nowitz Photography/Apa Publications
Cliff’s Variety
Continue south on Castro. This tightly packed commercial strip largely caters to the gay community and is devoid of retail chains. Instead, look for quirky longtime neighborhood outposts such as Cliff’s Variety 7 [map] (479 Castro Street; www.cliffsvariety.com; Mon–Fri 9am–8pm, Sat 9.30am–8pm, Sun 11am–6pm), a unique hardware store with aisles of tools, craft supplies, fancy-dress outfits, and home-decoration items.
To end the walk, turn left on 18th Street and walk 3 blocks to Samovar Tea Lounge 1, or return to Market Street and turn right to recharge at Café Flore 2.