The Story Of Halloween In The Castro, As Told By The Sisters Of Perpetual Indulgence

“Halloween has always been a high gay holiday,” wrote Sister Roma from Paris, where she was hosting the PinkX Gay Video Awards this past weekend. And for decades, the place to be on that most holy of “high gay holidays" was the Castro, which drew thousands of visitors each year for its Halloween celebrations, dating back to the Cliff's Variety costume contest in the '40s. 

Sister Roma, along with her fellow Sister Dana van Iquity, recounted how the Sisters of Perpetual Indulgence turned an emergency earthquake fundraising effort into one of the city's most iconic events.

The year was 1989, and San Francisco was still quivering in the aftermath of the Loma Prieta earthquake two weeks before. “Everyone was very shook up,” said Sister Dana.

To help raise money for the mayor’s relief fund, a small group of sisters— including Sister Vicious Power Hungry Bitch, Sister Dana Van Iquity, Sister Blanche deRoot, Sister Luscious Lashes, Sister Roma and Sister Dana—took ladders, bullhorns and buckets to the annual Halloween celebration in the Castro to collect money.

“We set it up in the middle of the Castro, and we just asked people to give a buck for charity,” said Sister Dana.

Halloween in the Castro (2005). | Photo: Shu Wu/Flickr

The evening was a success. “After collecting more than $10,000 in one night,” wrote Sister Roma, “we realized that this gathering was a huge resource of untapped income for the community.” The following year, the sisters joined up with the San Francisco Gay Men’s Chorus and Community United Against Violence to officially organize Halloween in the Castro.

Over the next five years, the Sisters brought together some of the best performers in the city, and hosted “the most spectacular costume contest ever seen,” added Sister Roma. According to the sisters, the costumes were "creative,” “over-the-top,” “campy,” “hilarious,” and “elaborate."

Sister Kitty Catalyst (left) and Sister Dana (right), Halloween party 2012. | Photo: Rusty Blazenhoff/Flickr

“Of course,” said Sister Dana, “there were a ton of drag queens: first-timers wobbling on their little heels. They’d never been in drag before, but Halloween gave them permission to let their inner queen out.” Proceeds in those years went to a number of charities, including the AIDS Emergency Fund.

(As a side note, Sister Dana provided us with some tips for anyone who’s planning to unveil “their inner queen” tonight. “Definitely practice walking in the heels, and don’t try to have nine-inch heels your first time,” she said. “And learn to walk up and down stairs"—she’s twice fallen down flights of stairs, and now prefers flats.)

Sister Roma (2014). | Photo: Doug Kaye/Flickr

Even though the annual street party was both beloved and bankable for the Sisters, attracting hundreds of thousands of people to the Castro, the Sisters' Halloween festivities came to an end in 1994.

According to Sister Dana, she witnessed a person running through the crowd with an actual chainsaw, and police confiscated AK-47s and arrested over 50 individuals. “That’s when we said ‘close it down.’ We don’t want [the Sisters] name identified with something that’s not safe.” (Halloween parties in the Castro continued without the Sisters until 2009, when the city put a halt to official events there, citing safety concerns.) 

Since then, the Sisters have hosted a number of Halloween events around San Francisco, ranging from the costume-mandatory HallowQueen to the family-friendly Children’s Halloween, which will be hosted later this afternoon. “We have family values, too,” laughed Sister Dana.

Halloween in the Castro has changed over the years, and even though many people, Sister Dana included, might find themselves feeling nostalgic today, they encourage celebrants not to be deterred by Halloween being on a Monday this year. 

“This is our high holy holiday,” said Sister Dana, “and it should be celebrated with gusto. Please be safe, but insane. And if you’re gonna go, go for it.”

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