San Francisco: Showtime in the Castro

As the curtain falls on San Francisco’s summer street fair season, the Castro kicks up its heels.

As summer draws to a close, so too does San Francisco’s street fair season. But not before one final block party.

The Castro Street Fair, now in its 46th year, promises to send summer out with a bang  with tens of thousands of people expected to converge on the iconic neighbourhood on October 6, the first Sunday of the month.

Started by legendary activist Harvey Milk in 1974 in response to the discriminatory policies of local merchants, the first Castro Street Fair attracted just 5,000 people.

Today it ranks as one of the most important festivals on the city’s LGBT calendar, alongside the annual Pride Festival and Parade.

It’s also held one week after the much-larger and much raunchier Folsom Street Fair, an eye-opening leather, rubber and BDSM event which attracts fetish enthusiasts in their droves, dressed in their bondage best of course.

The Castro Street Fair is mild in comparison: an all-day party and cultural event that includes artisan foods from local eateries, unique art and fashion, drag shows, live music and open-air dancing in the commercial heart of the Castro.

It’s a free event that asks for a $5 to $10 donation at the gate, almost all of which goes back to not-for-profit beneficiaries. Nearly $1.5 million has been given back to the  community since 1998.

Funds also go towards maintaining the huge rainbow-colored flag that reigns supreme on a 70-foot flagpole at Harvey Milk Plaza.

The 20 x 30 foot rainbow flag.

Over the years the fair, one of the oldest street celebrations in San Francisco, has morphed along with the gay community.

In the 1980s, after Harvey Milk’s assassination and as AIDS began wreaking havoc, the fair provided a welcome reprieve from near-constant anxiety and grieving.

Now the fair serves as a family reunion of sorts as the demographics of San Francisco’s 94114 ZIP code starts to grey. The locals may be older, but they still know how to party.

The Castro Street Fair extends for four blocks along 18th St, where you will find multiple drink booths and a massive food court at the intersection of 18th and Diamond Streets.

Along the way you’ll see rainbow flags and banners hung on most of the buildings as local businesses and residents alike kick their heels up.

The iconic Twin Peaks Tavern

At the start of Castro Street, near Market St, you’ll find the iconic Twin Peaks Tavern (401 Castro St) – the bar that has sat both literally and figuratively at the centre of San Francisco’s gay rights movement and community, and now has official landmark status.

Twin Peaks Tavern, which first opened in 1935, is believed to be the first gay bar in the USA to feature full-length, open plate glass windows that let its patrons look out.

The art deco Castro Theatre

Wander down the hill to the art deco Castro Theatre (429 Castro St) – one of the few remaining movie theaters from the 1920s that is still in operation.

While most visitors only stop to take photos of its huge, red neon sign that illuminates at night, its interior is far more interesting.

On either side of the stage are large organ grills. There’s an art deco chandelier that dates back to 1937. And two dramatic staircases lead to the mezzanine and balcony, highlighted by large mirrors framed in gold.

Rainbow crossing outside Harvey’s.

Get a selfie at the iconic rainbow crossing at Castro and 20thand then drop into Harvey’s Restaurant & Bar (500 Castro St) for a bite to eat or a cocktail or two. It’s also the perfect spot for people-watching.

Anchor Oyster Bar.

Further along Castro you’ll find Anchor Oyster Bar (579 Castro St), a small locally owned seafood bar that serves the freshest oysters, shellfish and cioppino around. 

On Fair Day, don’t forget to duck into the Dance Alley at 18th and Collingwood Streets to get your groove on, or wander down to 18th and Noe Streets to join the line stepping fun at the Sundance Saloon.

Local DJs and bands will front the Main Stage at 19th St and other smaller stages throughout the fair.

Many local businesses along Market St will also be celebrating the Castro Street Fair, so be sure to check them out, too.

Q Bar on Castro

When the sun goes down, Castro Street really kicks up its heels with dozens of neighbourhood bars partying well into the night.

Q Bar (456 Castro Street), Mix Bar (4086 18thSt) and Toad Hall (4146 18thSt) are among the most popular. Lookout Bar (3600 16th St) is always heaving.

When you’re done and dusted, you can always rely on Orphan Andy’s (3991 17th St) for a late night bite to eat before jumping on the F Line.  It’s a 24-hour, old-school diner and a staple of the Castro.

How to Get There

The Castro Street Fair runs from 11am-6pm on Sunday October 6, 2019.

From downtown, the Castro is easy to reach on public transport. Just take the K, L, M or T Muni Metro trains and exit at the Castro St Station. You’ll be in the heart of the action.

For a more scenic ride, take the F Line street car from Fisherman’s Wharf along the Embarcadero and up Market Street to the Castro.

  • Blog updated on September 13, 2019.

Find Out More

Castro Street Fair

© 2019 Bernard O’Riordan (Travel Instinct). All Rights Reserved 


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