Three miles and 11 minutes into the Fixt of Fury 2 alleycat bike race, I wobble through the first checkpoint, get a signature, and push off. I’m trailing a pack of guys toward Hong Kong Carryout, on East Capitol Street, where we have to find out the price of an egg roll. “I have no fucking clue where we are,” says a courier named Patrick Sudduth, as we run smack into the Brentwood rail yards. “I’m from Baltimore.”

Just after 10 p.m., a scrum of fifty-odd messengers and wannabes—fortified by National Bohemian and shots of Jim Beam—had pushed off outside Looking Glass Lounge, a bar on Georgia Avenue NW. The true masochists among them were still smoking as they Velcroed their bike cleats. Steve Spencer, a courier and tonight’s race director, handed out copies of the manifest—a list of nine checkpoints to hit between here and the finish line, from a bulletproof-glassed carryout near the D.C. Armory to the National Cathedral.

“Be safe, because”—what, exactly, is unintelligible—“is not worth dying over,” Spencer announced. Then it was 4-3-2-1 and we were off, the veteran couriers screaming down Georgia Avenue and the rest of us cranking like hell, trying to keep up.

Alleycats were born in Toronto in the late 1980s, the halcyon days of messenger culture. “They were literally sprints through the alleys, which, in Toronto, go on for miles,” explains Shawn Blumenfeld, a retired D.C. messenger. Courses are designed to wend through the city, with each rider devising her own way to hit all the checkpoints. There’s no rule against pulling out your iPhone, but the best messengers win on mental maps—and nerve—alone.

But fewer and fewer riders fit that description. Blumenfeld says that when he retired in 2004, “There were four hundred active bike messengers in D.C. Now there’s a hundred.” E-filing has gutted the business. “In the mid-nineties, there was competition for real money.” A crack messenger might have made $1,000 a week. “Now, I gotta guess they’re pulling in $500, tops.” As more couriers succumb to the scan-and-email future, alleycats keep the diaspora alive.

The first checkpoint is on 12th Street NE, and almost immediately, half the peloton peels off down a side street. You’d think it would be easy enough to hang on to the back wheel of an experienced rider. But then, you’d be wrong. The flashing red lights quickly divide again. Soon, I’m sucking air alone.

As it happens, this isn’t my first group ride of the day. Twelve hours earlier, I’d joined another group of pedal-pushers—this one decked out in enough reflector strips and red blinkies to worry an epileptic—for the Washington Area Bicycle Association’s Ride for Responsibility.

If alleycats are the last gasp of a badass, golden-age bike culture, the WABA responsibility ride is a pretty good harbinger of what comes next: rosy-cheeked adult commuters, their suit pants tucked into dark socks, cruising along dedicated bike lanes toward federal office jobs. Three percent of Washingtonians who commute to work do so by bike, the fifth highest rate in the country. In this world, letting your freak flag fly means wearing that ankle cuff with pride, brother.

The morning ride, designed to encourage bike commuters to set a good example by obeying traffic lights and yielding to pedestrians, was notably short on adrenaline—and velocity. “Stopping!” yells Greg Billing, WABA’s outreach and advocacy coordinator, at a yellow light. The phalanx of riders behind him waits patiently in the bike lane. “No reason to push it,” he says.

This peloton obeys each and every stop sign. “That means a complete stop,” Billing reminds us. In Chinatown, we patiently weave around the pedestrians and jay-walkers. It was here, in 2010, that a bicyclist—riding on the sidewalk—struck an elderly couple, killing the man. “The guy rode off and was never heard from again,” D.C. Bike Ambassador Daniel Hoagland tells me. A homicidal cyclist is the kind of man-bites-dog story that editors love. “We were anxious to get out in front of the ‘bicyclists kill people’ idea,” Hoagland says—hence the Ride for Responsibility.

An hour later, after a group photo outside the White House, we pedal up the 15th Street NW cycletrack toward Adams Morgan. Hoagland is hauling a trailer with the sign, “Bike Lanes Aren’t Parking Spaces.” We lock up in front of a café and un-muss our helmet hair. Verdict: success; friendly honks; good, clean optics. “This ride might do more for making sure that bikes are respected on the roadway than last night’s Critical Mass ride,” muses Hoagland. Riders check their brakes, ding their bells, and soberly head home.

Bike messengers, unlike commuters, are still divided over the utility of brakes; many of the riders in Fixt of Fury 2 make do without. Instead, they weave and skid through intersections, dodging buses and howling profanities, their tires smoking. Logan Stommel, a mechanic turned Marine, hops the median on New York Avenue NE and nearly wipes his map across the hood of an oncoming car. It’s relevant to point out that he’s wearing headphones—dubstep, metal—instead of a helmet. What would his poor mother think? What would any of our poor mothers think?

Hong Kong Carryout’s egg rolls cost $1.15, tax included.

At the Titanic Memorial on the Southwest waterfront, the marshals make us do the Leo/Kate pose over the Potomac River before signing our manifests. Then it’s two miles straight up 7th Street, into the heart of Chinatown, to copy down the hanzi on a Subway sandwich shop’s sign. We churn across the National Mall, fighting an awful wind, the Capitol and monuments looming huge and pale in the sky’s black blanket. “Push it!” yells Sudduth, as we hurtle through a red light, kissing a taxi’s bumper.

We lose Stommel for a while, but he catches us in Dupont Circle. “One of the guys we were riding with just took out a pedestrian and the cops stopped him,” he says. Later, we find out that the rider fractured his face and got carted off in an ambulance.

A straight shot down M Street NW, through Georgetown’s Saturday night circus, to a checkpoint at the Key Bridge, followed by three molar-rattling miles along the canal towpath. It’s now midnight.

Around Mile 21, we climb straight up from the river to the National Cathedral. With just one gear, the effort is lung crushing; the pre-race cigarettes aren’t doing anyone any favors. On the descent to the finish line, in Mount Pleasant, Stommel jumps a curb to avoid a bus, blowing his tire. “Shit, I’m down!” he yells. The group doesn’t even slow.

We sprint up Mount Pleasant Street like it’s the Champs-Élysées, standing on our pedals, tongues lolling. Bikes are strewn about the finish line in front of a group house. The winners have already tapped the keg.

Inside, I find Mike Pearce, an 11-year vet who took top honors. Was it something about his gear ratio? His frame weight? “You don’t have to be the fastest if you know the city better,” he says, smiling. Over in Northeast, “if you take one wrong turn around there you’ll be like, ‘Whoa, where the fuck am I?’ A few guys accidently rode to Anacostia tonight.”

Pearce will be back at work on Monday, riding like an absolute banshee. Don’t expect to see him in a bike lane.