Halloween celebrations will officially return to San Francisco’s Castro District at the end of October after a 16-year absence, but while there will be plenty of dressing up in the streets, people shouldn’t expect nighttime crowds numbering in the tens of thousands.
On Oct. 28 and 29, the famously LGBTQ-friendly neighborhood will become home to daytime block parties, costume contests and a spooky movie marathon. Hosted by the Castro Merchants Association in cooperation with the Civic Joy Fund, it’s meant to be a two-day PG-rated party for all, with the Castro Theatre screening a quadruple feature consisting of Death Becomes Her, Edward Scissorhands, Hocus Pocus and The Rocky Horror Picture Show, with free admission for anyone in costume.
“It’s one of those things that’s old but new, so we don’t know how many people are going to come out for it,” said Terry Asten Bennett, the association’s president and the proprietor of Cliff’s Variety Store. “We’re going have DJs, cornhole, a plethora of photo booths, crafting, face-painting, a pie-eating contest and pumpkin carving. Apparently, there will be a sugar overload this weekend.”
Long before the neighborhood became a gay mecca, Cliff’s Variety was the nucleus of Halloween in the Castro (then largely known as Eureka Valley). Asten Bennett’s own family helped get it all going in the 1940s.
“Pie-eating contests have been part of our tradition since my great-grandfather started Halloween in the Castro,” she told The Standard. “This will be for who can eat the fastest—not the most.”
Over time, Halloween in the Castro became something of a “Queer High Holy Day” nearly on par with Pride Weekend. Eventually, the Sisters of Perpetual Indulgence, the city’s beloved troupe of drag nuns, took over, and Halloween drew enormous crowds and effectively closed off the entire Castro. In 1989, two weeks after the Loma Prieta earthquake, the Sisters used the event to raise recovery funds.
However, in 2006, a mass shooting wounded nine people. Halloween 2007 brought a massive police presence, but the party was canceled the following year—and every year after. Smaller events have taken place here and there, but nothing nearly as ambitious as before.
This year, there will be costume contests for kids, pets and adults—expect a lot of neon-clad gay men looking like Ryan Gosling’s Ken from Barbie—with Sister Roma and Sister Morticia hosting.
It’s a daytime-into-early-evening affair, Asten Bennett said, although some of the neighborhood’s many bars requested grants to mount activations of their own. Lookout, for instance, will have a Ghostbusters-themed party called the "Ectozone," with DJs, drinks specials, a "Slimer" in the bar and a Stay-Puft Marshmallow Man on the roof.
The Castro had a difficult time recovering from the pandemic and has lately become a hotbed for late-night break-ins, but the neighborhood has shown new signs of life, with longtime bar Badlands recently reopening after a three-year absence and Italian wine bar The Rustic moving into the longtime Chow space on Church Street.
The neighborhood has also had a long history in the fight for sexual liberation, something that may collide with a family-friendly event in a very only-in-San-Francisco fashion.
“That’s the reality that we’re just used to here,” Asten Bennett said. “There’s the three guys that always walk around with no clothes on, and it is what it is.”
