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    Are the Sisters of Perpetual Indulgence the Queens of Halloween?

    Sister Roma

    By Sister Roma–

    The short answer to the question posed in the title of this piece is yes! I know for a fact that the Sisters are indeed the Queens of Halloween because I was there when we got our crowns.  

    Before we dive in, it’s important to acknowledge that Halloween has always been considered a high holy holiday for many of us in the LGBTQ community. Let’s be honest, we’re theatrical. We love to dress up. We love horror, camp, and glamour. Don’t believe me? Ask Peaches Christ; she’s made a career of it. We love playing with gender and making political statements. Most of all, we have an innate ability to make literally anything sexy. There’s something about being dressed as a sexy school teacher and flirting with a sexy zombie that speaks to our soul.

    Halloween celebrations in San Francisco have raged for decades with roots to Polk Street as far back as the 1960s when many of us were forced to live our lives in the closet. Halloween was the one night a year they could “come out” to play and revel in their queerness.

    By the 1980s, Halloween had moved to the Castro where tens of thousands of costumed revelers crowded the bars and filled the streets. These nighttime street parties happened organically and were wildly popular. 

    Halloween Castro 2005

    Jump to October 17, 1989. At 5:04 pm, San Francisco was shaken to the core by the Loma Prieta earthquake. Now you might be wondering what this has to do with Halloween. Have I suffered a stroke in mid-article? No, girl, let me explain. A couple weeks later, on Halloween night, the Sisters decided to take action. A handful of us brought step ladders, buckets, and bullhorns out onto Castro Street to collect money for then-Mayor Art Agnos’ Earthquake Relief Fund. Many of the revelers that night dropped bottle caps and cigarette butts into our buckets—but many, many more dropped cash—a lot of it! By the end of the night, we had raised over $10,000. It was then that we realized Halloween in the Castro was a huge untapped resource for fundraising in our community.

    The following year, the Sisters officially produced Halloween in the Castro. We added two flatbed truck stages with live entertainment, DJs, and a spectacular costume contest. From 1990 to 1995, the Sisters reigned as the Queens of Halloween. We invited community partners to work the gates to raise money for important causes like Community United Against Violence (CUAV), and HIV/AIDS. Halloween in the Castro became our largest annual fundraiser and one of the most popular events in San Francisco, attracting crowds estimated to be over 300,000. (This also started the tradition of collecting donations at gates to street fairs we still see today.)

    Sister Dana leading the Children’s Halloween Parade in the Castro (2006)

    As the event grew so did the attention from others outside our community who came to the Castro to gawk, harass, and even violently attack LGBTQ people. Sadly, the Sisters were forced to cancel our beloved event because it became too dangerous. The safety of our community has always been our priority. 

    For years, LGBTQ people and our allies have continued to gather in the Castro to celebrate our high holy holiday, as we should. That’s why I’m excited to share that this year the Sisters have joined forces with Manny Yekutiel, the Civic Joy Fund, Another Planet Entertainment (A.P.E.), Supervisor Rafael Mandleman’s office, and the Castro Merchants to officially produce Halloween in the Castro! 

    Castro 2006

    This year’s celebration will take place on Saturday, October 28, from noon to midnight. Over 40 Castro venues will participate in Halloween-themed events including a $5 Horror Movie Marathon hosted by the Castro Theater. The neighborhood will be decorated and alive with drag brunches, face painting, fortune telling, storytime, trick-or-treating, drink specials, and much more!

    The entire event will culminate with the world-famous Halloween Costume Contest hosted by the Sisters inside the Castro Theater at 8 pm. Costumes get in free and cash prizes will be awarded in four categories: Spookiest, Sexiest, Funniest, and Best Overall. We’ve got surprise guests, special performances, and a few more tricks (or treats) up our sleeves. Your $5 charitable donation includes admission to a 10 pm showing of The Rocky Horror Picture Show immediately following the contest. I can’t think of a more iconic San Francisco Halloween experience!

    Let’s make this our safest Halloween yet. It’s important to note that there will be no street closure. Please visit the bars or come to the theater after dark. Don’t go out alone, stay alert, and try not to overindulge. It’s time to bring back Halloween in the Castro and keep it in the family. See you there!

    Sister Roma, “The Most Photographed Nun in the World,” is an activist, fundraiser, and icon. For 36 years she has been one of the of most outspoken and highly visible members of the Sisters of Perpetual Indulgence.

    Arts & Entertainment
    Published on October 20, 2023