United States of America

Pride of the City

Celebrate San Francisco’s oldest, wildest Halloween tradition in the Castro.

I don’t want to go. It isn’t that I’m not intrigued. As a wholehearted aficionado of all things Halloween, I have envisioned myself among the madness in the Castro hundreds of times, wearing some absurd costume, trying on a different life for a night.

No, it’s because I’ve heard Halloween in the Castro just isn’t the same any more. After a string of annual violence that culminated in a 2006 shooting, the city of San Francisco aggressively moved to put an end to the famous 60-year-old holiday festival. Tonight the police are reported to be ready for a full-scale riot along Castro Street, so I’m not exactly feeling the free-spirited enthusiasm I once had for the event. Besides, Halloween is alive and well and running rampant right outside my hotel in Fillmore, even though the late October sun is still sitting high over the Golden City.

But downstairs, as I walk through the hotel lobby to get a closer look at the madness that’s simmering out on the street, I’m stopped by some fellow travellers who are jonesing to get over to the real celebration.

“What do you mean you’re not interested?” they ask incredulously. “It’s Halloween. In the Castro.”

What can I say? They’re right. Every keen traveller in San Francisco during Halloween knows that a trip to the Castro is a box ripe for the ticking. Before I know it, I’m with the pack on the 24 bus, heading southwest through the city’s rolling, vibrating streets. Not far off, a fog-laden dusk seeps in, as if the gods have just cranked on the smoke machine for the night’s main act.

The blocks fade as the bus ascends to some of the highest points in the city. Throngs of mini-skirted she-devils, bloody vampires, naughty schoolgirls and drunken Jack Sparrows filter on and off, all caught up in their adopted caricatures and evening itineraries.

At Golden Gate Avenue I look east between the legions of pastel Victorians and catch a glimpse of the Financial District’s glass and concrete fingers rising up from the banks of an inky San Francisco Bay. Dipping down again for a moment we pass Haight Street and I can only imagine the characters amassing a few blocks up at Ashbury. But throughout this entertaining, alcohol-fuelled procession, I’m only getting excited for what lies ahead – this, I hope, is nothing compared to that.

You don’t begin your first Castro experience from anywhere else but at 17th and Market, exactly where we step off the bus. Standing at Harvey Milk Plaza beneath the lazily swaying rainbow pride flag, I finally get a glimpse of the mythical, maniacal Halloween celebration.

At its zenith in the early 2000s, Halloween in the Castro was a festival teasing the fringes of absolute chaos. Although the famed event began in the 1940s as a modest neighbourhood costume party, by the 1970s it had become Mecca for the LGBTQIA+ community worldwide. Crowd numbers soared into the hundreds of thousands. But by the time things came to a head in 2006, the crowd of some 300,000 revellers was an uninterrupted cross-section of humanity. Bay Area gangbangers bumped elbows with gay men wearing nothing but their birthday suits. So when gunfire rang out, leaving nine bystanders seriously wounded, city officials immediately called for drastic changes to the festival. In the years that followed, Castro Street was closed down, street performances were banned and police presence increased five-fold.

Despite some drastic changes, however, I can see the famed celebration has lost none of its lustre. Standing beneath the red neon glow of the Castro Theatre, it’s quite clear that, around these parts, the she-devil is considered a lazy pursuit, Jack Sparrow an indefensible cliché. No longer outnumbered by the thousands of uncostumed party crashers of years past, the Castro’s most flamboyant specimens float along, popping in and out of bars and swaggering as if the sidewalk were a fashion week catwalk. Like they originally were in the 1970s, these men and women – the heart and soul of the Castro – are once again the centre of attention.

It is here, at the theatre, that I meet a flighty Art Deco drag queen shining with make-up and pearls that immediately make me sure this ain’t her first rodeo. “Darlin’, I haven’t missed Halloween in the Castro for six years!” she says to me as she bounces about, posing for passers-by’s cameras.

When I ask her what motivates her to keep dressing up so lavishly, she is predictably succinct. “It’s tradition!” she yelps, then falls into a lively conversation with a couple of other drag queens.

Soon we are consumed in the growing procession of more drag queens, sailors, priests, nuns, the Super Mario Bros and Carol from Where the Wild Things Are. The sidewalks reach maximum capacity and queues begin snaking from the many notorious bars and restaurants lining Castro Street. Things inside and out are heating up.

Near Cafe Mystique we run into a virtual wall of lively spectators. Camera flashes pop without pause as laughter and cheers drown out the sounds of celebration further along. I crane my neck above the sea of shoulders to see a pair of the Castro’s famous nudists casually chatting just the same as two co-workers would after a long day at the office. While I’ve seen my fair shake of costumes in my day, I have never witnessed this: the fabled birthday suit – the boldest of them all.

In a bizarre way, we all agree that our tour of Halloween in the Castro is complete. With the night well on its way to morning, and the neighbourhood bars the domain of only the colourful local residents, we hop on the 24 bus and head back to Fillmore, where the lure of live jazz is too much to pass up.

At close to 2am we are standing in the Sheba Piano Lounge. Along Fillmore Street, Halloween is still alive, though it’s the she-devils, schoolgirls, vampires and Jack Sparrows – rather than the drag queens – that reign supreme.

In the low-lit purple and pink tones of the lounge, patrons are busy talking about the sort of things folks talk about in the smallest hours of the night. Behind the bar, lounge owner Netsanet Alemayehu and another bartender turn out cocktails while holding multiple conversations all without missing a beat. I lean in and catch Alemayehu just before the stroke of two, when bars in San Francisco must legally cut off the booze. She obliges my last call and slides me a couple of red wines. With the amount of people still lingering about she reckons she’ll stay open until three. Despite working the closing shift more often than not, Alemayehu doesn’t look tired. Rather she looks like one of her own customers, smoothed by the daily musical therapy cascading from the house grand piano and its players on the other side of the lounge.

Outside on the Sheba’s verandah, cigarette smoke hangs thick in the cold autumn air as the sounds of jazz filter out from the dim doorways of Yoshi’s, the Fillmore and the Boom Boom Room down the street. The sidewalks host the occasional inebriated vampire or kitty cat, but one is left with the feeling that this scene is merely the offspring of the ever-flamboyant Castro District, truly the grand-daddy of all San Fran Halloween celebrations.

As the last notes of San Francisco’s finest jazz disappear with closing time, we make our way back to the hotel for a few hours of sleep. In the lobby, Elvis has passed out on the couch. Next to him is a fairy. This Halloween, it seems, has been a success.

The next morning gives way to a lucid autumn day. The famous fog bank hangs abated out over a green, lolling Pacific Ocean. I have made my way to one of San Francisco’s most overlooked neighbourhoods, Ocean Beach. Before me, cold slabs of raw ocean swell detonate on distant sand banks. Behind me rises a grid of Victorians. Beyond that, the big smoke.

For days I have walked the streets of San Francisco’s most famous areas: Haight and Ashbury, the Mission, Fisherman’s Wharf, Japantown, Pacific Heights, Nob Hill and, finally, the Castro. Since Friday I have found myself tangled up in one Halloween bash after another.

Now that the holiday has met its end, I’m actually feeling refreshed. Then I’m approached by a vampire who hands me a flyer for some sort of final Halloween hoorah tonight. I blame the Castro for this. But I wouldn’t miss this chance to celebrate my favourite holiday just one last time.