E-Mail This Article to a Friend Urban cowboys The underground city-bike-racing scene hits the streets of Boston BY MATTHEW SHAER

FOR ALL INTENTS and purposes, this June’s R7 Rally* bike race is Boston’s worst-kept secret.

Hundreds of cyclists know about it; 200 of them — from as far afield as Japan — are expected to race. And while no major media outlet will likely cover the R7 (so far, only the Phoenix has even noted its existence), the race is a pretty big deal. It will wind its way from an undisclosed location in Boston to an undisclosed location in New York with a fleet of support vehicles. It will award prizes to the winners and give a brightly colored jersey to each day’s leader. It will throw a party at each stop and provide accommodations for all participants. So why don’t the organizers of the race want you there?

Here’s the rub: the whole damn thing — from the course the racers will follow to the event’s complete disregard for state and city statutes — is illegal. The R7 is the latest in a series of urban-cycling events that are revitalizing Boston’s bike-messenger culture — on legs of shaky legality and with a dash of good old-fashioned criminality thrown in.

"In this city you have to be careful," says Craig Roth, age 34, a veteran Hub cyclist and one of the minds behind the R7. "In New York, the police have bigger fish to fry than messengers riding through the streets. In Boston it’s something they’d be happy to be involved in."

This is a supposition no one involved with the race is willing to test. Almost every road the racers will follow between Boston and New York is officially off-limits for cyclists: remember, no farm equipment, animals, or bicycles are allowed on the highway. For this reason, the R7 is being publicized only through a small handful of Web pages and by word of mouth. So unless you’re a committed urban cyclist with a taste for fast, scary city riding, you’ve probably heard nothing about it.

The race’s organizers say they can’t remember anything on the scale of the R7 being attempted before. Following the stage format of professional road races like the Tour de France, the R7 is split into seven separate events, from sprints through Boston, Providence, and New Haven to long-distance endurance pushes and a time trial in Manhattan. Eschewing solo efforts for the comfort and relative benefits of team tactics, racers will compete in groups and arrive in New York in time for many of them to race all over again, this time in the Bike Messenger World Championships, the single-largest testing ground for urban-riding specialists and the annual focal point of courier culture around the world.

But for Boston, the R7 Rally is much more than the sum of these parts; it’s a way for area organizers to prove their mettle in larger events in neighboring New York. And perhaps more important, it’s a litmus test of just how far urban riding has come in the traditionally staid Hub — and how far it might go.

CITY, RALLY, messenger, urban: these are all terms used to describe a similar kind of bicycle riding; namely, the kind in busy traffic. Although not all urban riders are current bike messengers, most are former couriers or have some association with the courier business. This is where the immediate similarities end. From city to city, from Somerville to Chinatown, urban riders blow all efforts to categorize them out of the water. Some wear monster masks to shock passing cars. Some wear tight-fitting road-cycling jerseys to help them go faster. Some are clean-cut. Some smoke cigarettes or pot. They cover their bodies, head to toe, with various tattoos and piercings, and regard their bodies as pure athletic instruments. Helmets are rare, gears rarer. They paint old Schwinns 16 different shades of orange to create an eyesore; they baby their vintage Italian road frames to the point of obsession — one rider explains, in earnest, that his ride "sleeps over his bed, so [he] can keep her company."

Urban riders train all afternoon to compete in various high-intensity, aerobic events like the R7. Most now ride on fixed-gear track bikes, with skinny tires and a single brake on the front wheel. Some ride with no brakes at all, pushing the frame to the side and using their legs to create a skid effect powerful enough to bring the bike to a halt. That particular skill is considered one of the purest forms of city riding in a sport where expression bordering on performance — from the outfits, to the gorilla masks, to the sharp risks taken in traffic — is everything.

"No one does the shit that we do — not as quickly, not as dangerously," says one Boston rider at an "underground" race. "And this brings us all together in a way that not everyone can understand." In the end, the shared danger may resemble the shared scars: everyone has a story to tell, everyone has a nasty cut from a cab door or passing bus, and everyone is ready to do it again, a little faster.

"I’ll do this until I get killed," says 51-year-old courier and spinning instructor Kevin Porter, "or until I die of old age." Porter, who’s been riding in Boston for 10 years, calls himself "Boston’s deadliest messenger"; he’s been involved, by his count, in more than 30 traffic accidents. None has been serious. "That," he insists, "has nothing to do with luck."

In the end, the disparate characters of the urban bike scene are bound together not only by their shared sense of daredevilry, but by participating in formal and informal riding events, from the Critical Mass — a ride that intentionally blocks traffic to bring public awareness to bicycle rights — to impromptu alley sprints. Nearly everyone who calls him- or herself an urban rider competes in one way or another, and nearly everyone who competes is thoroughly committed to pissing someone off.

*The name of the race has been changed to protect organizers and riders.