[This story was written in 2003 shortly after these events. It is being posted in 2026 when San Francisco is a very different city. Nothing stays the same, alas, but this may still have meaning even if only as an archeological artifact of a different City in a different day. Wherever the town may be now and in future, this is part of where it came from and part of how it got that way.]
San Francisco likes its holidays as much as the next city, maybe more than some. Its residents like to party and have been known to block off streets to celebrate such things as Chinese New Year, “regular” New Year, Gay Pride, street fairs and even humble neighborhood block parties. Traditional holidays are usually given a bye and you can actually find parking spaces on Christmas Day, Thanksgiving and the Fourth of July.
But there are two regular parties which are held with no sponsor, no organization and no real planning and they turn out to have inordinate impact on the City. One is the monthly celebration (or curse, or swarm) of bicyclists in the streets, a rolling party of anywhere between 200 and several thousand bike riders, called Critical Mass. It is always held on the last Friday of each month. For October, 2003, it fell on Friday the 31st, the day of the other great anarchistic street party: Halloween.
Most people don’t ride bikes and so hate Critical Mass on principle. What they know of it they learn from watching television, reading the papers or, if they are truly unlucky, getting stuck in the traffic jams it causes. Mass always begins at the foot of Market Street, some time around 6 PM. There are no leaders, no organizers, no plan and no route. There is no one to apply for a parade permit and no one to take out liability insurance. It is by monthly “accident” that so many people gather in this one spot to take an evening ride. They mill around in the plaza, greeting friends, handing out leaflets, staring and posing until, at some unplanned but inevitable moment, after much whooping and hollering, they reach, well, critical mass and start riding off in some direction.
Mass may begin in any direction on a road leading away from the plaza at the foot of Market. No one knows why, when or how it will start. It just does. Everyone is happy to ride along but no one, including the riders at the front, knows where they are going. Sometimes people try to “urge” the ride to have a destination. It almost never works. The mass of cyclists meander through the downtown streets, turning onto this block or that, heading up that hill, through this tunnel, around that square, with little sense of direction and no seeming purpose other than to enjoy a moment of car free riding.
It’s car free because cars trying to drive on or across any street on which the mass is moving are inevitably stuck until the mass passes by. Even when a light turns red the mass keeps going through. To ensure no one gets hurt, some outriders will “cork” a cross street, standing astride their bikes before the blocked traffic to ensure no one moves forward and endangers the riders. It’s actually more efficient to block the streets and let the whole mass move through but drivers under appreciate this aspect of traffic science and sit on their horns. Riders perversely take this to be a supportive cheer and so happily wave and cheer back at the drivers. Pedestrians and tourists, point and smile and wave or jeer. It is quite a show from the sidewalk. News helicopters circle overhead.
Some drivers are honestly supportive and honk and wave and smile and get the joke, even though it is on them. But most drivers just fume, believing, as drivers are wont to do, that it is all the “other” cars and bike riders who are causing traffic jams, not they themselves. A happy bit of solipsistic nonsense which is enshrined in the very notion of owning and driving a car in America.
Unlike Critical Mass, Halloween is known to most people from their childhood. They made or bought costumes, strolled through their neighborhood knocking on doors and saying “Trick or Treat” with no real intent of making good the explicit, extortionate threat. Candy is distributed, costumes admired, parents hovering nearby. Sometimes people threw more traditional parties, even ducking for apples or pulling taffy, carving pumpkins and such. But usually, once adolescence has passed, it is time to leave Halloween to younger folk and move on. It is one of the least commercialized of the “big” holidays.
But in San Francisco, around the time most kids are returned home from Trick or Treating by their parents and trundled off to bed, another crowd starts to gather for a Halloween party. Again, there are no sponsors, no plan, no organization. All that is known is where it is going to be: Castro and Market Streets, better know in latter days as “The Castro.”
This party is a huge costume street party. For decades people have gathered, in costume, from all over the City, to stroll, dance, display and gawk at the creative energies of their fellow citizens. To be sure, the gay community, traditionally concentrated in the Castro, contributes a great deal of the party goers, but people of all orientations come from far away to join in. The only “rule” never enforced, and too often ignored, is to show up in a costume of some sort.
It is a grand and public opportunity to do something outrageous and know that you will fit in. There are so many men wearing dresses that it almost ceases to be noteworthy, even when beards and hairy chests are fetchingly exposed. There are sailors, dwarves and gnomes, characters from recent movies and classics, monsters, ghouls, politicians, harlots, fancy girls, fancy boys, babies, crones, policemen, real policemen, firemen, prisoners, punks, hippies, hipsters, rabbis, monks, nuns and seemingly every variation and combination of them all. It is jaw droppingly hilarious and with the beat of volunteer music pouring out of windows or traveling boom boxes the dancing and frolicking goes on late into the night, spilling into all the side streets, as upwards of 300,000 people gather to party in a city whose inhabitants number only slightly more than double that number.
Some years back City Hall, in its finite wisdom, had tried to disable the Castro party by sponsoring an official San Francisco Halloween party in the huge plaza before City Hall itself. The idea was to woo the partyers to a place where more order could be maintained and less disruption occur. Needless to say, most people ignored it entirely and after several years of watching the “official” partyers leave and stroll up Market to where it was really going down, the City gave up and just blocked streets in the Castro.
In 2003, for the first time in memory, these two parties coincided. Critical Mass starts early so it got the first shot off. Thousands of bikers showed up at Justin Herman Plaza, aka “Pee Wee Herman” Plaza, almost all of them in costume. Variety does not even begin to cover the outlandish getups that were in evidence. There were hazmat teams, punks, monsters, biker chicks, tigers, cows, dogs, birds, ninjas, brides, apes, garbage men, vampires, dudes in suits, Pee Wee Herman, Waldo, bike helmets of all sorts festooned with odd objects, bags over heads, goggles, on eyes, the Cat in the Hat, nurses, accident victims, sailors, welders, pioneers gals, and more often than not just weird shit that people put on and over their bodies before setting out for an evening ride, including one fellow whose T-shirt, commissioned just for this Halloween ride, read, “Two Wheels, One Dark Lord.”
All of this eventually became mobile as the ride randomly but inevitably started for the evening. To say that it meandered would be an understatement. Heading first up Market Street it veered into the Financial District, swerved into the Union Square shopping district, wandered through the Tenderloin, bumped back onto Market, rolled up along Van Ness, around City Hall and so on. All this to the cacophony of bike bells, horns, boom boxes, cheers, whoops and yelps to drivers and passers by, car horns blaring, V-signs and waves, shaken fists, shaken heads and upraised middle fingers. It was as though the Castro Street party itself was doing a wake up introduction to the neighborhoods of the city by carrying the party to them.
It was too early for much to be going on in the Castro but the ride finally made it up Market Street, passing a marching band and a Taiko group, also headed for the party, to arrive at the street barricades demarking the party area. This year the police decided to limit alcohol at the Castro Street Halloween party and so barricades were more in evidence than in previous years.
Here the ride turned aside and began meandering through the Mission neighborhood, steadily losing riders, as is usually the case, until it wound to its inevitable conclusion. Here the remaining riders dispersed to their dinners or their own holiday celebrations. For people who like to party in the streets, wear silly costumes, ride bikes and feel normal about it all, it was a perfect night.