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The Castro

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History: The stretch of Market Street running through Eureka Valley was too steep for horses, keeping this neighborhood remote until the 1880s, when a wave of settlers chugged in on steam-powered streetcars and created a melting-pot neighborhood of immigrant families sometimes dubbed little Scandinavia. Most Holy Redeemer Church opened in 1901 and became the heart of the neighborhood, complete with a convent whose nuns taught at the grammar school. In the late ’60s, San Francisco’s gay population, encouraged by the burgeoning gay rights movement to live openly and create a community, began settling in the Castro’s fading (and relatively cheap at the time) Queen Anne Victorians. By the ’70s, the neighborhood was America’s most prominent gay village. Most Holy Redeemer is still here, dubbing itself San Francisco’s inclusive Catholic parish.

Don’t Miss: The centerpiece of the Castro is the lavish art deco Castro Theatre, whose unmissable red neon sign helped give the neighborhood its name. Check the schedule for film festival showings, double features, and boisterous sing-along nights. At the intersection of Market and Castro Streets, across the street from one of the world’s largest rainbow flags, is Twin Peaks Tavern, the city’s oldest gay bar and the first to have windows that allowed a view of its interior from the street (old-school gay bars blacked out their windows to protect the anonymity of their clients). If you’re seeking a high-energy gay bar scene, try dancing at the Badlands or stopping in to see the local characters at 440 Castro. For an even deeper dive into neighborhood history, visit the GLBT History Museum or to Magnet, a one-stop health clinic for gay men combined with a culture center that features local artwork and hosts seminars on local history. If you’re looking for sustenance to get you up Sanchez Street to the top of Dolores Heights or over to dog-friendly Duboce Park, indulge in coffee flights paired with excellent baked goods at the new Hearth Coffee Roasters. Both Frances and Starbelly restaurants offer the best in California-inspired cuisine, while the ultra-casual sandwich shop Ike’s Place always has a line. Woodhouse Fish Company offers dollar oysters on Tuesdays, but do those top the ones at nearby Anchor Oyster Bar? You’ll have to be the judge. Orphan Andy’s burgers and fries are conveniently on offer 24 hours a day for those in need of a bite after partying the night away. Once you’re sated, find a souvenir of this distinctly San Francisco neighborhood among the rare and hard-to-find jewelry, collectibles, and antiques at Brand X Antiques. Tim Flint, its owner for 25 years, can answer any questions you have on the neighborhood’s history and fill you in on the local gossip.