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Castro Street Fair is a testament to Harvey Milk’s legacy

3 min read
Saul Sugarman

Harvey Milk made important strides for us even before he became the first openly gay supervisor elected to office in San Francisco. He started Castro Street Fair some 49 years ago to promote queer businesses that faced hostilities and challenges, like his own Castro Camera on 575 Castro Street. I think he would be proud of his efforts today.

Each LGBTQ+ festival carries a different vibe in San Francisco: Pride is our annual national spotlight on the local community, and likewise, Folsom brings us widespread attention and celebration within sex, kink, fetish, and shared intimacy spaces. Dore Alley is like a little sibling of Folsom, and Castro Street Fair likewise appeals more to a local crowd. The latter’s always been just a little racy with nudists and some sporting fetish wear, but also quite family friendly with many local vendors, dance parties, sidewalk art, and just happy people.

The streets along Castro and 18th, up to 19th, and down on Market felt so packed, but also slightly more tame than perhaps last year. Castro Street Fair fell on a day both Hardly Strictly and Portola music festivals took place, which we all guessed might have been why we had a little more space to breathe. But just a little.

I personally like to attend because it’s a good time to be seen by a cross section of the LGBTQ+ community that perhaps I missed at a house party I couldn’t attend, or concert, or other festival. And I wear something very noticeable, so people can find me, of course.

Also spotted Sunday:

  • Cheer SF serving up performance after performance with backflips and basket catches. Throwing someone over concrete gave me a few shakes but no one got hurt.
  • Beautiful artwork in booths, on sidewalks, and in queer coloring books.
  • Drag shows by Obsidienne Obsurd, Mojo Carter, and Landa Lakes that kept my interest and adoration even though I’m a rare gay who doesn’t follow a ton of drag.
  • Children! Little girls complimenting my dress and tipping drag queens.
  • An always lovely Devlin Shand of Queer Arts Featured, carrying on Harvey’s legacy by occupying that old Castro Camera spot with appropriate tenacity and lifting up other LGBTQ creators. And giving smiles to everyone, even though Shand I’ve no doubt hadn’t stopped working for seven days straight and stood in impossibly tall heels.
  • Pre-pandemic faces I thought vanished after 2020 but are still in San Francisco, still thriving, still happy to see me, and still supporting local community even if our social circles have all changed.
  • Love, joy, and fiercely fabulous outfits.

Saul Sugarman is editor in chief of The Bold Italic.

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Last Update: November 06, 2025

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