If only the Mexican land barons and European homesteaders who built the Castro district could see it — and the price of its real estate — today. What was once dairy farms and dirt roads is now one of the city's most vibrant and cohesive communities, saturated with stylish shops and bars so popular that patrons spill out onto the street.
Irish, German, and Scandinavian immigrants came to the outskirts of San Francisco in search of cheap land, which became bona fide suburbs after 1887 when the Market Street Cable Railway linked Eureka Valley (as the Castro was then called) with the rest of the city. Thanks to these homesteaders, who built large, handsome Victorian houses for their large families, today's residents have someplace to pour their money, and the vast majority of the neighborhood's classic homes have been lovingly and artfully restored.
Eureka Valley remained a quiet, working-class neighborhood until the postwar era, when large numbers of people started fleeing the city for the "suburbs." Finally, in the 1960s and '70s, gay men began buying the charming old Victorians at relatively low prices ($20,000-$40,000), and the neighborhood was soon named for its busiest thoroughfare, Castro Street.
The activism of the '60s and '70s forged a community with sizable political and economic power, and when the historic Twin Peaks bar at Market and Castro streets was built with floor-to-ceiling windows, most took it as a sign that Castro residents were secure in their gay identity. There were, however, tense and sometimes violent clashes with the police, and the assassination in 1978 of openly gay San Francisco Supervisor Harvey Milk was a turning point in the community's history. Milk's death and the impact of AIDS brought the community together and made activists of almost everyone; the Castro became not just open but celebratory about its thriving gay and lesbian population.
Today, the Castro's identity is itself a tourist attraction, beckoning throngs of pilgrims and revelers from all over the world. Since the introduction of the F Market street car, shuttling unsuspecting Midwestern families down from Fisherman's Wharf, denizens have been lamenting the demise and dilution of the gayest spot on earth. Yet the unabated proliferation of shops selling, ahem, adult accessories and sporting neon signs touting "Lube 4 Less" tips off even the most untrained eye to the deeply entrenched community here.
Castro Street Fair: In late October, the city's longest-running street fair (founded by Harvey Milk himself) features booming music on multiple stages, crafts, drag shows, comedy, food, plenty of drink and more people than you knew existed. Website.
Halloween was once one of the biggest and most extravagant festivals of its kind anywhere, with Castro, 18th and Market Streets closed off for the festivities. After multiple shootings and stabbings in 2006 however, the city cracked down on the party and withdrew official support. Recent Halloween nights have been peaceful but a shadow of their former bacchanalian selves.
San Francisco Pride Month: The last Sunday in June, Market Street becomes a throbbing, queer sea of human beings for this annual display of LGBT power. The parade is always led by the SF Women's Motorcycle Contingent, the celebration at Civic Center will fulfill your every need for rainbow and pink-triangle bric-a-brac, and the plethora of pre- and post-parade parties will satisfy even hard-core circuit boys. The Saturday before the big parade, the Mission and Castro districts are taken over by lesbians from all walks of life, as well as their children, pets and musical instruments for the SF Dyke March (and Rally).
Frameline SF International Lesbian and Gay Film Festival: June is truly the most exciting time of year in the Castro, when this venerable fest attracts filmmakers from around the world for ten days of screenings, parties, and discussion about queer film. .
No matter what's playing, buy a ticket to see a movie at the Castro Theatre (429 Castro St.). Hearing its Mighty Wurlitzer Organ alone is worth the price of admission. Prepare to be amazed at the art-deco, Moorish and otherwise lavish combination of interior designs that is The Castro.
Affiliated with the Universal Fellowship of Metropolitan Community Churches, the Metropolitan Community Church San Francisco (150 Eureka St.) is the second-oldest lesbian and gay congregation in the United States. It's a vibrant and progressive community of faith for gay, lesbian, bisexual and transgender people in San Francisco, and the building that houses the church also houses many, many other community organizations that support everyone from teens to the homeless.
Smack in the middle of the Castro, Magnet (4122 18th St.) takes a truly holistic approach to gay men's physical, mental and sexual health, but this is no sterile clinic. Yes, you can get anonymous STD and HIV testing, but Magnet also offers counseling, classes, seminars, performance arts and even game nights where gay men can socialize, interact and learn in a judgment-free zone.
Twin Peaks (410 Castro St., website) gather our village elders. And for this it is known by an appalling epithet: the Glass Coffin. Be that as it may, men of all ages may enter and be welcomed.
The Edge (4149 18th St.) is neighborhood bar par excellence, with zero attitude, manly men and stiff drinks; small wonder so many community groups choose it as a spot to convene.
Midnight Sun (4067 18th St.), a line of clean-cut young bucks extends down the block. Inside, enormous TV screens are everywhere the eye darts. Most of the guys here are only slight variations on a single (in this case, a buttoned-down and buttoned-up) theme, but it's a comfortable place to watch TV with other men.
The Mix (4086 18th St.)
Moby Dick (4049 18th St.) — scarcely a block apart, both quintessential Castro haunts — can be largely interchangeable, yet each is endearing and accessible, no-fuss joints where you can go have a beer and shoot pool and rub elbows with the local hoi polloi. If only The Edge (see above) also began with the same letter, we'd have a complete set.
Cafe du Nord (2170 Market St.) carries its history as a former speakeasy like a torch. Located literally underneath the historic Swedish American Building, it'd be a sublime place for a secret rendezvous if it weren't so dang popular. Nightly live music ranges from the best in swing to an adventurously booked experimental lounge night.
The Mint (1942 Market St.) offers this city's best and, not coincidentally, queerest karaoke experience. With more than 3,000 (free) song selections, a refreshingly diverse crowd and an almost familylike atmosphere, this popular nightspot inevitably provides feel-good fun for those who like their fave tunes de/reconstructed by amateurs, wanna-bes, occasional real-life rockers and the far, far too drunk.
The Lookout (3600 16th St.) features great views and a welcoming atmosphere. Nestled in the heart of the Castro, Lookout has everything you need for a good time from nightly DJs, to trivia nights, plus a weekly drag queen show.