"We're always living in fear of the day it rains," says Castro Street Fair Board President Juan Garcia. "The moment it started it raining, we were all looking at each other. We knew it was doomed."

So it was with last October’s Castro Street Fair, which as a result of several factors, including some unseasonal rain for early October, pulled in just a fraction of the door donation and beer sales that it typically does, creating a financial crisis for the fair’s board of directors after several tight years. It was the 43rd annual outing for the neighborhood festival founded by Harvey Milk that pre-dates Folsom Street Fair but is now dwarfed by it, traditionally scheduled for the Sunday following Folsom, and some on the board, including Garcia, thought it could very well be the last.

In addition to having to live in Folsom’s shadow and appeal to a gay community that may well be partied out after a long summer, the Castro Street Fair has also had to share a date with the third day of Hardly Strictly Bluegrass over the last decade, with just a few years when they didn’t conflict. The result, despite this typically being the busiest day of the year for many neighborhood businesses, is an event that has come to play second and third fiddle, and due to a lack of sponsors — many of whom commit themselves to Folsom — is no longer the dependable fundraising force it once was for community organizations that donate their volunteer time in exchange for annual grants.

"There were years we used to give away $70,000 or $80,000,” Garcia says. “This year we barely made it to $38,000, and that was with a $15,000 bailout from the city." And while festival-goers may assume that neighborhood fairs like this one are put on by the city, that's not true — and the city actually charges the organizers for police presence, and for the re-routing of Muni lines on the day of the fair. "We wipe out our bank account every year," Garcia says, adding that some smaller organizations depend on the street fair's annual donation just to survive.

Board treasurer Jon Murray spoke to SF Weekly this week about the possibility of canceling the fair, saying that outgoing Supervisor Scott Wiener assisted in getting them the bailout funds from through the Arts Commission and the Mayor’s Office of Workforce and Economic Development, but it came with the caveat that the fair’s board needs to prove in 2017 that they can make the numbers work on their own. The fair’s executive director Fred Lopez tells the Weekly that the first step will be to hire a consultant “to start pounding the pavement to get sponsorships in the door.”

Garcia says he’s been advocating for bigger sponsors for years, and notes that SF Pride, a far larger annual event, ran into similar financial trouble several years ago. "We have to get sponsors who help us pay to produce the fair without having to dip in to our fundraising money," he says, noting also that they are just a board of ten people who volunteer their time, whereas SFPride and Folsom both have paid staffs and dozens of people organizing each of their events.

He knows, too, that the fair not only needs sunny weather, it needs more of a draw for the community in terms of entertainment. “What people don’t understand is that all of our performers perform for free,” he explains. "My challenge every year is getting the best entertainment that's appropriate to the event, and who will agree to donate their time. I basically have to convince them all to perform for free in exchange for exposure. It's always a big puzzle slash dance."

Early commitments from sponsors, and bigger sponsorships, Garcia says, will allow him to book performers who wouldn’t agree to perform pro bono, and who are of the caliber booked for Folsom — and paying entertainers is something that will also have to change in the fair's by-laws, because it's never been done. And, he suggests forging partnerships with businesses in the neighborhood, like bars, which benefit from the one-day boom in foot traffic that the fair provides.

Another possibility for the fair in 2017 will be a smaller footprint that focuses more on Castro Street, he says, as well as more drink options besides beer, which could happen through beverage sponsorships.

"Everything about the fair is going to change," Garcia says. "It's not sustainable the way it's being done."

An added bonus for 2017 is that Folsom Street Fair falls two weeks before Hardly Strictly Bluegrass, meaning that Sunday October 1 is free and clear for Castro Street Fair to go on without a major conflicting event.

In the end, it’s a collection of community organizations that are affected the most by the fair’s financial ups and downs, including groups like Castro Cares, Castro Community on Patrol, the Imperial Council of San Francisco, and the SF Gay Men’s Chorus.

I leave you with some footage, which you can view here courtesy of the GLBT Historical Society, of the Castro Street Fair in its third year, 1976.