You know you’re in the lively Castro neighborhood when you see a giant rainbow flag soaring in the wind. The flag stands in the main square, Harvey Milk Plaza, named for the slain civil rights leader who served as the state’s first openly gay politician. The subject of the critically acclaimed film “Milk” starring Sean Penn, he owned a camera shop on the district’s main thoroughfare, Castro Street. Full of quaint Victorians and sunny, tree-lined streets, the Castro is one of the oldest (and presently the largest) gay neighborhoods in the country, having survived a tragic hit during the 1980s AIDS epidemic. Today the attractive area buzzes with energy at all hours.
The Castro is easily accessible via the F-Market historic streetcar line, which goes from Fisherman’s Wharf and along the waterfront to downtown and up Market Street. For context on the neighborhood’s rich history of activism, start with a visit to the GLBT History Museum or join an informative walking tour such as the Cruisin’ the Castro walk. This month marks the unveiling of a new sidewalk tribute titled Rainbow Honor Walk, which celebrates its 25th year this month. The growing series of 20 plaques is dedicated to noteworthy LGBT figures in the arts, sciences, politics and sports. You’ll also spot the landmark Castro Theatre, a magnificent Art Deco movie palace with over 1,400 seats and a giant neon sign symbolic of the neighborhood. The venue shows classic and cult films and hosts campy sing-alongs to musicals such as “The Sound of Music” and “Frozen.”
The Castro is a hub for casual, affordable eats. On Market Street, you’ll find Super Duper, a local burger chain that uses fresh, organic and local ingredients. The soft serve cones and spiked shakes are both hits. Down on 18th Street is Kasa Indian Eatery, San Francisco’s modern take on Indian street food, where kati rolls are the go-to here. Chile Pies (Sweet & Savory) serves New Mexican grub—hearty pot pies, stews and salads as well as dessert pies and ice cream.
If you’re looking to dine and linger, Frances serves the world-class, California cuisine that put San Francisco on the foodie map. (Reservations aren’t easy to snag, so come early or prepare to wait for a seat in the tiny restaurant.) At Canela, the Spanish tapas and wine list are excellent, and the atmosphere is dim and romantic. Stylish Starbelly is known for hearty fare and patio seating.
If a sugar or caffeine fix is in order, the neighborhood has options like the little Hot Cookie shop which serves craveable cookies (the most popular variety is racy-shaped macaroon). Coffee shops include the successful local chain Philz, where each cup is hand-poured to order (and the barista will add any milk or sweetener requested), and the chic new Reveille Coffee Co., which makes one of the best cappuccinos in the city as well as tasty food. Tea drinkers will want to spend some time at Samovar Tea Lounge, an elegant sanctuary of zen that offers a worldly tea service with international small plates.
A prime destination for revelry, you’ll find a gay bar with thumping beats at any time of the day or night in this part of town (and maybe spot a drag queen or two). Some of the most popular are The Lookout, Q Bar, Toad Hall and Badlands. The vibe is mellower at Twin Peaks Tavern, frequented by a mature crowd. The neighborhood watering hole was the country’s first gay bar to boast glass windows and is dubbed a historic site. You’ll find a mass of mixed clientele enjoying the craft cocktails and pool tables at Churchill. On Market Street, Blackbird mixes artisan drinks in a sleek setting, yet the vibe is decidedly casual.
You’ll spot retail giants like Pottery Barn, but the hood is also home to a number of independent boutiques, including a number of cleverly named adult novelty stores. Other shops worth a look include the lovely and friendly Church Street Flowers and Urban Flowers, the high-end Sui Generis consignment stores, Books Inc. and the Human Rights Campaign Action Center & Store (at the original location of Harvey Milk’s camera store). Anything but an ordinary hardware store, Cliff’s Variety (in business since 1936) also sells puzzles, toys, art supplies and feather boas. GQ-approved heritage menswear brand Unionmade and a men’s-only Levi’s shop outfit the stylish gentleman, while A&G Merch stocks quirky-hip home goods.