They gathered at twilight. By 8:30 p.m. on Saturday, April 15, nearly 80 bicycle couriers had jammed into Dupont Circle, awaiting the start of the First Annual D.C. Outlaw Courier Race.

Though increasingly common in other cities with heavy courier traffic, the race was the first of its kind in Washington: a nine-mile trek in the dark through eight checkpoints and back to the Circle. “This is an unsanctioned event,” admitted race organizer and veteran courier Urk, who like most of his colleagues, goes by his biker nickname. “We’ve got no insurance, and everybody enters at their own risk.”

Urk started the race by jumping onto the lip of the bubbling fountain and shouting out the first checkpoint: “The Chinese Embassy, 2300 Connecticut.” Seconds earlier, every bike had been pointed in a different direction. Suddenly, in the same fluid motion you see in a school of fish when a shark approaches, the bikes aligned and streamed out of the circle, flowing past both sides of the underpass opening and heading northwest up Connecticut.

Sidewalk pedestrians looked up in confusion. One man strolling past a bar stared with bug-eyed wonder. A motorist honked, angry to find himself behind a clump of cyclists. “Fuck off!” one of the couriers yelled back. Then he and the rest of the pack accelerated, running red lights all the way.

Like outlaw races in other cities, this one simulated a courier’s day on the job. Contestants not only had to hit the eight checkpoints, but get their manifests stamped at each. They used all their law-flouting tricks, including “snatching”—grabbing hold of a car.

Whoever was monitoring the Chinese Embassy’s surveillance cameras must have seen a disturbing tableau: 80 couriers storming up Connecticut in fairly tight formation, then swarming around the man who rubber-stamped their manifest sheets.

As they got their stamps, the racers were told that their next stop was the National Research Council on 2001 Wisconsin Ave. NW (having to plan their routes as they rode made the race that much more like a day on the job). In this case, there was no consensus about the best route; some couriers turned west onto Kalorama Road, others backtracked down Connecticut, and some continued north across the Taft Bridge.

The race, Urk said, was inspired by his most disturbing experience as a courier: a violent confrontation with a mob of street vendors. While he fought with his back to a wall, three of his fellow bicycle couriers rode by. None stopped or called for help.

“That shouldn’t happen,” he said. “Couriers need to back each other up at any cost. Without that, we’re just a bunch of individual people running out into the streets with the whole city against us.” Since the demise of d.c. space—once the high temple of local courier culture—the profession has splintered, and Urk hoped that a race would pull it back together.

His confrontation also illustrates the Washington police’s hostility toward couriers. “It was a rainy day in January,” Urk recalled. “These two ladies negligently jaywalked across the street in front of me.” There was a near-accident, followed by an angry exchange of words that attracted an interloper. “The two women happened to be black, I happen to be white. All of a sudden I’m Whitey the Oppressor in the view of this random street vigilante. This guy starts getting in my face.” Urk couldn’t get rid of him, and before he knew it Vigilante Man was joined by a half-dozen street vendors.

Urk tried his radio, but was in what couriers call a “black hole”—a spot where tall buildings block transmission. Vigilante Man disappeared around a corner, returned with a full Pepsi bottle, and threw it at Urk’s back, breaking two ribs and cracking another. When Urk tried to defend himself with his bicycle lock, his shoulder was pulled out of its socket.

To add insult to injury, Urk said, when the police finally arrived they threatened to arrest him. “They told me I had been loud and disruptive in the street. Couriers are always cast as the culprits.”

That was Urk’s last day on the job. His injuries forced him to retire, at age 27, after 13 years as a bicycle courier. Among other things, the race was a way of ending his career on an upbeat note.

But wouldn’t an outlaw race just reinforce the couriers’ negative image as reckless lawbreakers? “I don’t think so,” Urk said. “It’s not going to affect many people. At 8 o’clock on a Saturday night, this town’s pretty much vacant of traffic.”

The atmosphere at the third checkpoint, Kennedy Center, was like that of a kids’ bike-tag game after curfew. While busloads of senior citizens lined up for the new Neil Simon play, race organizers huddled surreptitiously at the edge of the dark parking lot, checking the progress of the race via walkie-talkie and keeping their eyes peeled for police.

The first contestant to arrive was Zack Doo-Doo, a big guy with a yellow ponytail. After getting his stamp, Doo-Doo spun around and cranked off in the direction of point No. 4, the Corcoran Gallery. Among those cheering him on was A.Z., a race organizer who talked about the complex relationship white-collar Washington has with its couriers. On one hand, there’s the bad reputation; on the other, that free-spiritedness.

“They want to love us, but they hate us too much,” A.Z. said, noting that when he’s making deliveries, elevator conversation inevitably turns to his job. On sunny days, everyone wishes they were out riding. On cold days, people express sympathy. A.Z.’s inevitable response: “It’s never a good day to work in an office.”

From the Corcoran, racers were sent to 807 Maine Ave. SW. Those who could resist the batter-fried aroma of Water Street’s seafood eateries then biked uphill to the U.S. Postal Service Headquarters at 475 L’Enfant Plaza SW. The man for whom that plaza was named might be pleased to hear that couriers from other cities like D.C.; its grid design makes it easy to navigate compared to cities like Toronto or San Francisco.

“It’s really quick,” said a dreadlocked Joe Dias, one of eight couriers from Toronto who drove down to be in the race. But unlike D.C., Dias added, the Toronto police at least try to make cyclists obey traffic laws. “I’m amazed—here they blow red lights right in front of the cops,” he said. “Man, if you did that in Toronto, they’d be on your ass.”

Just a few minutes after Dias had left checkpoint No. 7 (the 12th Street loading-dock entrance for Columbia Square and the Warner Theater), heading for the final stop (Techworld Plaza), word came over the walk ie-talkie that Doo-Doo had arrived back at Dupont Circle, making him the first-place winner. His total time: a little more than 40 minutes.

As the rest of the pack straggled in, Doo-Doo recounted his ride to a semicircle of admiring rookies. The most dangerous obstacles, he said, were the tourists along Wisconsin Avenue in Georgetown. Dias beat all other out-of-towners. In the women’s division, a third-year courier named Sheba took first prize. “Just one big happy family,” she said, looking around at the boisterous mob.

The also-rans had stories to tell as well. One rider videotaped the race by duct-taping a camcorder to his helmet. One group took a wrong turn and ended up riding half a mile on Interstate 295. A few other racers collided with each other, resulting in ugly-looking scrapes. But overall, there were no serious injuries and no trouble with the police.

After Doo-Doo had held court for about 30 minutes, several couriers grabbed him and threw him into the fountain. Dias looked on approvingly and observed, “That’s a new custom, man.”