HTML tags: A street sign in the Castro neighborhood of San Francisco. The annual Castro Street Fair, the brainchild of Harvey Milk, the first openly gay person in California to be elected to public office, was first held in 1974. 
There’s no denying that San Francisco knows how to throw a good party, regardless of the location, climate or time of day. Throughout the summer, several neighborhoods host their own annual street fairs to celebrate their unique cultures, complete with local vendors, artists, musicians and experiences that showcase their individuality.
And then, there’s the grand finale — the Castro Street Fair, arguably the biggest and wildest of them all. So brace yourself and let go of your judgments (and maybe a few layers of clothing) as you plunge into our ultimate guide ahead of the 49th annual Castro Street Fair, which will take place in October in the Castro District.
When is the Castro Street Fair?
The Castro Street Fair takes place the first Sunday of October. The party kicks off around 11 a.m. and officially winds down around 6 p.m. (although there are plenty of after parties). In October 2023, the first Sunday falls on Oct. 1, so mark your calendar.
Now, we know what you’re thinking, “Why is there a ‘summer street fair’ on the first Sunday in October? ” If you’re not familiar with San Francisco and its gloriously confusing microclimates, let me explain. In San Francisco, we don’t typically have four traditional seasons. Instead, we have pockets of truly gorgeous weather that interrupt our usual routine of temperate weather.
So when San Franciscans think of summertime, or at least summertime weather, we usually think of the end of September towards the middle of October, not during “June Gloom,” “No-Sky July” or “Fogust.” That’s why the first Sunday in October is the perfect time to throw a wild neighborhood block party like the Castro Street Fair, which certainly will feature some scantily clad attendees.
San Francisco Supervisor Harvey Milk shakes hands with Mayor George Moscone at a press conference in this 1970s file photo.
How long has the Castro Street Fair been around?
Before we dive into what to expect at this year’s Castro Street Fair, it’s important to explore its rich history. To do so, we reached out to Andrew Shaffer, Director of Development and Communications at the GLBT Historical Society and Museum for a quick history lesson. “The Castro Street Fair was started in 1974 by Harvey Milk at a time when the neighborhood was experiencing significant change,” said Shaffer. Although the Castro is now seen as the main queer district in San Francisco, that wasn’t always the case — in the 1960s and ’70s, the neighborhood was only just starting to get that reputation. “The intention was to provide a way for the new LGBTQ residents, and the folks who had been in the neighborhood for longer, to connect and meet each other.”
Harvey Milk, one of the first openly gay people to be elected into public office in the United States when he won a seat on the San Francisco Board of Supervisors in 1977, lived by core values of coming out of the shadows, fighting for equality and celebrating our community’s beautiful diversity. These continue to resonate throughout the street fair to this day. That’s why the street fair not only features performances, street food and spaces for local artists, but also booths for political organizations, nonprofits and volunteer groups dedicated to the ongoing fight for LGBTQ rights.
It’s worth noting the Castro Street Fair is the lone remaining annual event in this vibrant neighborhood where main roads and intersections, including Castro Street, are shut down to allow locals, merchants and organizations to celebrate in the streets. Halloween in the Castro, another long-standing street event dating back to the 1940s, was discontinued after a shooting in 2006. Similarly, Pink Saturday, the Castro’s huge SF Pride street party, ended its yearly event in 2016. The retirement of these events, coupled with the ongoing political climate targeting LGBTQ rights, serves as a reminder of why the Castro Street Fair feels as sacred in 2023 as it did when Harvey Milk first introduced it in the ’70s.