Sitting on the tailgate of my buddy's beat-up pickup truck, I dig through a box of ratty-ass race numbers that are now in their sixth year of usage. Rusty safety pins are stuck through them, and their corners are shredded from being attached to the sweaty jerseys of multiple dirt racers. I'm collecting rumpled five-dollar bills from eager would-be bike racers in exchange for the glory of participating in the 17th annual Urban Outlaw Cyclocross Cross-Dressing Series. It’s an event organized by my bike team, dfL, on the down low (though there are somehow always hundreds of racers at our start lines).

The numbers are going out faster than the money is coming in because we have a rule that anyone dressed in drag (or anyone wearing a dress, for that matter) races for free. City-living, dirt-race-loving cyclists aren't the richest group of athletes out there, so I’m surrounded by cross-dressers.

dfL, by the way, stands for Dead Fucking Last, a sailing term the team ironically re-appropriated. Why the sarcasm? Many of the men and women involved race at a professional level — although most of them eschew the rules, regulations, and bowing down to corporate sponsors that an established team imposes.

Cyclocross is essentially a combination of road and mountain biking. Part of its draw is that it’s so damn difficult. We racers take our sport seriously, which is why it's so funny to see these tough guys wearing dresses.


Only in San Francisco, right? Our cycling crew is dyed-in-the-wool SF. The original team was composed of native-born guys (now in their forties) who formed the group in the early 1980s. They claim we're the second-longest-active cycling team in San Francisco, after the Olympic Club. The founders have only gotten stronger as they've aged; hardened into manly jerky through their years of crashing along on the first handmade mountain bikes down Mount Tamalpais with Gary Fisher himself.

There are women on our team, too: many of us are “new blood,” originally introduced to the team through dating someone on it, and there’s also one woman who didn’t have to get “jumped in,” but joined on her own merits. She’s fast as hell; one of the best female cyclists in California. My husband and I met at our Urban Outlaw Cyclocross Series in 2006. He calls us “more of a gang than a team."

Are you totally lost? Don't yet understand what a "cyclocross" is? Let's step it back a notch.

Cyclocross (often referred to as simply "'cross") originated in Europe in the 1960s as a way for European professional road racers to stay fit during their off-season. Nasty weather is no deterrent for enthusiasts; the fouler and messier the conditions, the more fun we have. In fact, San Franciscan cyclocrossers often complain about the sunny weather we get this time of year. Our Indian summer coincides with the start of our season, which goes from October through January. On rainy race days, we sport crazy-eyed, sludge-faced smiles, crossing the finish line dripping; high on endorphins, and on life.

The courses are designed to force you to dismount from your bicycle multiple times during the race. The route generally includes both paved and dirt surfaces, as well as barriers: 16- to 18-inch wooden boards to be barreled toward at full speed (18 to 20 mph for the elite men "A" racers). Then said boards are leapt over while lifting the bike in your hands. There are also "run-ups," which are short, nearly vertical hills that you must dismount for, then run up while hoisting your bike over your shoulder and digging your toes into the elements. Imagine the view from behind when over 200 racers in short skirts are scrambling up the backside of McLaren Park, elbowing each other to gain one place in position!

Really good courses might include sweeping turns around knobby tree roots, sand pits or beach sections, and knee-deep mud bogs. The racer who completes the most laps (which are generally between one and two miles long) in the allotted time period (30 minutes for beginning women to 60 minutes for the "Elite A's," the professional racers) wins. Because competitions are comparatively short, cyclocrossers go pukingly hard.

The level of athletic ferocity is especially amusing to watch at this evening’s event, where, due to an injury, I am on the sidelines after handing out numbers. The kids at the skate park jeer at a grown man in a flowered skinsuit and a tutu kicking at his bike, nearly in tears, after getting a flat tire in a deep rut and pulling out of the race.


While races can be done on a mountain bike, most serious competitors own cyclocross-specific rides. These have dropped handlebars and lightweight frames like road bikes, but also sport narrow, knobby tires for better traction, and cantilever (mountain bike–style) brakes. These brakes are less susceptible to getting clogged with debris during the optimal "all-weather" (read: absolutely miserable) race conditions.

Without having witnessed or, better yet, participated in this weird-looking sport, one that resembles nothing so much as a muddy ballet, you might wonder why in the world folks would want to subject themselves to a heap of abject misery and anaerobic suffering. Why would they take a perfectly good (and most likely highly expensive) custom-made bicycle and run around in the mud with it on their shoulders?

Because that's what cyclocross is all about.

And don’t expect us to make it easy for you if you actually manage to find out where, and when, one of the dfL races takes place. We’ll call you a nerd if you don’t wear a dress, and if you do, we’ll post a photo of you in it — covered in sweat and snot — on the Internet. We play dirty like that.


Our Urban Outlaw series is a weekly "warm up" that leads into the real season: the NCNCA (Northern California Nevada Cycling Association) races, sanctioned competitions that lead to a national and world championship. If you're looking to get into cyclocross, either as a spectator or as a racer, the single-speed world championship race will be held in San Francisco for the first time ever on November 20. As if cyclocross didn't sound hard enough already, this world-class race only allows entrants to run a bike with one gear. That means no shifting down like a sissy on the steep bits.

While cyclocross is still a specialized niche, it is growing in popularity, especially here in San Francisco. The four-part Pilarcitos race series takes place mainly in Golden Gate Park. Pilarcitos is actually legally sanctioned, which means that you'll be paying around $40 to participate. But when you face-plant while trying to bunny-hop a log by Stow Lake, there will be EMTs to bandage your wounds, instead of the group of beer-can-throwing hecklers found at the Urban Outlaw series.

As for the dfL races, you have to know someone who knows someone to find out where the start line is, and what the start time is. It’s kind of like an underground rave, but on bikes. The Freewheel at Hayes and Central is sometimes at liberty to divulge information about our races...