Editor’s note: Using a bicycle for transportation on the streets of New York City can be an intimidating, and downright dangerous, endeavor. The Bloomberg administration is working to make the city more bike-friendly – through newly designated bike-only lanes, to cite the most visible example. But how bike-friendly can a city be if its premier grassroots cycling event operates in an atmosphere of police hostility? That’s one question that occurred to self-described “accidental anarchist” Stuart Post, a 48-year-old resident of the Gramercy Park area, who joined last month’s Critical Mass bike ride.

Begun in San Francisco in 1992, Critical Mass is a deliberately leaderless happening (thus its anarchist cred): a regularly occurring, yet informal, group bike ride. These days it’s taking place in hundreds of cities around the globe. It started up in Manhattan in 1993; currently it leaves from Union Square Park at around 7 p.m. on the last Friday of every month, destination unknown. “Because I went on the ride, I was able to get used to riding in traffic,” says Barbara Ross, spokeswoman for the bicycling and environmental group Time’s Up! Acclimating to city streets is something the administration presumably would support. But, Ross said, “Our feeling is that since 2004 the city has been trying to stop the ride, or at least the NYPD [has].” On Aug. 27, 2004, just days before the last Republican National Convention opened here, the ride took place with thousands of participants – and mass arrests by the police.

Four years later, when asked if the city has an official stance on Critical Mass, neither the Department of Transportation nor the NYPD would articulate one. In terms of policy, however, chief NYPD spokesman Paul Browne wrote this in an e-mail: “Groups of 50, whether cyclists or pedestrians or whatever, require permits under the law. Permits allow groups to do things that would otherwise be illegal, such as bikes taking all lanes or traffic, or running lights – if the permit provided for it.” Regarding an incident described below, Browne wrote: “Officers who observed violations on Friday, such as running lights, stopped cyclists in the vicinity and issued summons. It may have appeared random to some, but it was for observed [traffic] violations.”

I’m a middle-class, middle-aged Manhattanite. I have a white-collar job in the nonprofit sector, vote in every election and primary – even the boring ones – never litter, own my apartment, and dutifully write checks to my favorite charities. Oh, and for the last 25 years or so, my primary mode of transportation has been my bicycle.

So I had mixed feelings when I stumbled across the Critical Mass ride on August 29 as I was cycling home from a Friday night dinner with friends on the Upper West Side. I’ve never been on one of these monthly rides: Sure I was curious, but my appetite for getting ticketed or arrested is pretty minimal. Yet my mounting annoyance over the NYPD’s ongoing, overkill response to the rides ever since the 2004 Republican Convention, combined with too-fresh disgust at the You Tube posting of a rookie cop slamming a random cyclist to the gutter during the July ride, got the better of me. I pedaled faster and caught up with the group at Seventh Avenue and Central Park South.

Although I was the only biker wearing seersucker shorts and a button-down shirt, I can’t say my fellow riders looked like the wild-eyed anarchists depicted in the media. Mostly, they seemed similar to the 20-something computer guys and design chicks working in my office building in DUMBO, Brooklyn. Wearing backpacks and messenger bags, they seemed to have come straight from the office. (It was refreshing to be in the midst of so many – maybe 200 or so – un-accessorized bikers; how nice to be reminded that cycling doesn’t require hundreds of dollars of spandex accessories.)

I was pleasantly surprised by everyone’s exemplary behavior: the cyclists stopped at every red light as about a half-dozen escort police officers on scooters rode patiently alongside or behind them to keep motorists at bay. I even noted friendly banter between a heavyset officer and a dreadlocked bike messenger-type. The ride was leisurely and meandering – down Seventh Avenue, east to Fifth, back over to Broadway and through Times Square. As we traveled through these heavily touristed areas, it was great to see the out-of-towners’ delighted reactions to our rolling crew: laughter, cheering, thumbs-up signs, digital cameras flashing away, smiles all around. What a great story for them to tell. Perhaps their snapshots of the impromptu bike parade will even encourage the folks back home to come to the Big Apple – with pocketfuls of Euros! – to experience such playful shenanigans for themselves.

The joy I felt to be surrounded by so many cyclists on a balmy late summer evening was exactly how I felt at Summer Streets, the successful Department of Transportation pilot that created a car-free Park Avenue on Saturday mornings in August. At both events, I got a brief but tantalizing glimpse of New York City achieving its full potential. So I happily rolled on, south through Herald Square, then to Chelsea, where the outdoor diners waved and clapped. Buzz from other riders indicated that Washington Square would be our final destination. Sounded good to me.

Yet something odd happened just south of 14th Street. The scooter cops riding “sweep” started tooting their horns and slowly made their way into our phalanx of bikers. While we were all stopped for a red light by St. Vincent’s Hospital, a displeased-looking police commander strode into the crosswalk and announced, “Okay, let’s ticket some of them.” The scooter cops surrounded the six closest riders and got out their pads. Shocked by this sudden flexing of law enforcement muscle, I got on the sidewalk to watch as most of the bikers pedaled off with the changing light, to complete the ride. Although I was joined by several other observers, none seemed particularly upset or surprised. Random ticketing is apparently NYPD standard practice at Critical Mass rides.

As a newbie, I felt sickened by this bait-and-switch: with no warning, our friendly motorcycle escorts were now ticketing cyclists and refusing to discuss their sudden shift with the unlucky prey. It was ironic to note that a dozen police scooters – how did their numbers double so quickly? – created more of an obstacle to traffic flow (which included a couple of ambulances rushing to St. Vincent’s) than the actual Critical Mass ride itself.

(Video of the ticketing can be viewed here.)

I’d had enough. I hopped back on my bike and headed home with a sick feeling in my stomach. Yes, my lovely and wholly unexpected group ride was now history. But I was far more bummed about the future of the city I so love. How could such small-minded bureaucratic pettiness be tolerated by the Bloomberg administration? And how did this behavior jibe with the mayor’s fierce advocacy of congestion pricing, sponsorship of Summer Streets, and creation of miles of new bike lanes? I had a sinking feeling that this jarringly mixed message – pat cyclists on the head with one hand and smack them in the face with the other – might seriously undermine Mayor Bloomberg’s vision of a green urban utopia.

Maybe I’m just too thin-skinned for this biker anarchist stuff, I thought…and headed off to bed.

– Stuart Post