Critical Mass riders execute a “Chicago Holdup” at the Wicker Park “Crotch” during the first monthly ride on September 5, 1997. Credit: James Warden

All manner of bikes were represented when about a thousand cyclists convened on Daley Plaza on the evening of September 29 to celebrate the 20th anniversary of Chicago’s monthly Critical Mass ride. There were flashy aluminum triathlon cycles, cruisers festooned with Christmas lights, and a “fat bike” with huge tires towing a little girl in a trailer. The Rat Patrol, a punk-rock bike gang known for their custom choppers, was there, including member Yly Coyote, a bearded young man with dreadlocks down to his butt, who was astride a roughly ten-foot-tall bike made of multiple frames welded together.

Photocopied route maps were passed out and longtime rider Todd Gee, looking like a dark-haired Mark Twain, stood at the base of the Picasso sculpture with a megaphone. Part of the plaza was blocked off in anticipation of the next day’s Beer and Bacon Classic. “Let’s get going,” Gee broadcasted. “It’s going to be hard to circle the Picasso, so let’s circle the block.”

Nowadays Daley Plaza is bounded on three sides by streets with protected bike lanes. At the northeast corner there’s a Divvy station, and across the street on Washington stands a Loop Link bus rapid transit station.

None of this infrastructure existed when the first of the monthly rides departed from the plaza on September 5, 1997. Critical Mass had started in San Francisco five years earlier as a combined bicycle parade and protest against car culture, with the movement eventually spreading to more than 300 cities around the globe.

Twenty years ago bike lanes and bike racks were rare in Chicago, and Critical Mass’s consciousness-raising rides deserve credit for helping to bring about major improvements to the built environment. The events also contributed to the cultural shift that led to Chicago’s percentage of commuters using bikes to get work more than tripling between 1997 and 2014.

The Active Transportation Alliance has acknowledged Critical Mass’s influence. “Once participants get a taste of the two-wheeled comradery that goes with the event and the feeling of riding city streets without being fearful of car traffic, people naturally [want] to get involved in making biking better,” wrote spokesman Ted Villaire in a blog post before the anniversary ride.

Chicago Critical Mass launched countless careers in bike advocacy and planning, including my own. I heard about a job opening at the Chicago Department of Transportation’s bike program during a Critical Mass-related bonfire party in 2001, which led to me spending the next five years getting some 3,500 bike racks installed citywide. Most of the CDOT bike lane planners at the time also got involved with cycling issues via the ride, and my predecessor as rack czar, a Masser named Eric Anderson, now serves as the bike/ped coordinator for Berkeley, California.

And then there are all the friendships and relationships that blossomed out of the ride and related events. I know of at least seven marriages and a dozen or so children that resulted from couples meeting through the Critical Mass scene.

Prior to 1997, attempts to stage a Critical Mass ride in Chicago drew a few dozen participants but failed to gain momentum. That summer I was working as a courier and booking the weekly Bike Messenger Night showcase at Phyllis’ Music Inn. The punk band Alkaline Trio played some of its earliest (and sloppiest) shows during the series. One night affordable housing advocate Michael Burton, an old co-op housemate of mine, stopped by Phyllis’ for an Old Style and met Jim Redd, a Web designer and poet whose son Adrian was a courier, and the two hatched the scheme for the rides that would depart from Daley Plaza. “We were going to assert a positive vision of how things could be in order to expose the current injustice of car-dominated public space,” Burton wrote in a essay about the experience five years later.

Tireless promotion by Burton and Redd paid off when some 200 cyclists convened on the plaza on September 5. Participants rode up Milwaukee Avenue to its six-way intersection with North and Damen in Wicker Park, stood in the middle of the junction blocking car traffic for a few minutes, and lifted their bikes over their heads in an exuberant gesture that became known as a “Chicago Holdup.”

Despite causing delays for motorists, and in contrast to the more confrontational San Francisco events, Chicago Critical Mass developed a decidedly friendly vibe, with founding parents like Burton encouraging riders to ring bells, wave, and yell “Happy Friday!” and “Thanks for waiting, folks!” to bystanders. That didn’t prevent run-ins with the law, however.

Credit: James Warden

I was the first person to spend the night in jail for participating in the monthly rides. During the fourth ride on a frigid December 26, as we pedaled through River North, an 18th Police District sergeant in a squad car ordered us over his PA system to get off the road. When I pulled over and asked the officer if we could ride a few more blocks to our destination, a bike-themed gallery show on Franklin Street, he noticed a CPD patch among the many Chicago-centric badges sewn on my messenger bag. He got out of the car, handcuffed me, threw my Trek in the trunk, and had me charged with impersonating a police officer. I can still smell the bologna sandwiches on white bread served in the lockup.

After that, 18th District police began randomly arresting a few riders whenever Critical Mass passed through their territory, in an apparent attempt to shut down the ride. Participants raised money for a legal defense fund, dubbed the “Cigar Box of Justice,” and after several cases were dismissed police seemed to relent. In fact, in subsequent years bike cops calmly escorted the ride and on occasion even “corked” cross traffic at intersections.

In the mid-2000s Redd moved to Ecuador, while Burton became a father and reduced his involvement with Critical Mass. Burton recently came out of retirement to plan and promote the 20th anniversary celebration that, in a bit of absurdism, he dubbed the 30th Anniversary Ride. He says he did this to acknowledge Chicago’s pre-1997 rides, noting, “The rounding up of numbers is a common practice among statisticians and those who rewrite history.”

Eric Anderson and a few other founding parents came back to town for the celebration. On the evening of the anniversary ride, after Todd Gee called for riders to circle the plaza, Anderson honked his huge, incredibly loud bulb horn—just like in the old days—bike bells rang out, and the ride was off.

Soon the swarm of cycles moved north on Dearborn toward the river. Riders were towing competing sound systems, playing everything from hip-hop to black metal to jazz. We turned east on Wacker, where riders flipped the bird to Trump Tower, then rolled south on Michigan as the sky began to turn mauve. As the group turned east on Randolph, a dozen bike cops brought up the rear.

While the map laid out a route that had the cyclists taking Columbus all the way south to Roosevelt, it turned out to be just a decoy route. Instead the herd took Monroe east and turned onto Lake Shore Drive, occupying all four southbound lanes, something the Mass hadn’t done for years. A northbound driver stopped at a red high-fived passing riders.

Chicago Critical Mass riders cross the Kennedy Expressway on Milwaukee Avenue during the first monthly ride on September 5, 1997.
Chicago Critical Mass riders cross the Kennedy Expressway on Milwaukee Avenue during the first monthly ride on September 5, 1997.Credit: James Warden

The crowd exited the drive before there was any friction with the police and rolled west on Roosevelt into a russet sunset with a breathtaking skyline view to the north. As the throng headed north on Michigan, a pair of young women wearing Muslim headscarves and sitting in a bus shelter waved, snapped photos, and shouted “Happy Friday!”

The Mass made its way northwest to Greektown, then rolled northeast again for a brief incursion into the Magnificent Mile, where cheering shoppers greeted the pack. After the Mass reached Wicker Park, I was disappointed that most riders didn’t stop in the middle of the North/Damen/Milwaukee “Crotch,” and practically no one did a Chicago Holdup. But old-timer Steve Timble (a former Reader employee) hoisted his road bike over his head with a broad grin.

The ultimate destination was the CHAOS (Chicago Homebrew Alchemists of Sud) Brew Club space near Grand and Western. Riders there were greeted with free beer, fire pits, and DJs spinning instrumental disco, house, and electro. Steven Lane, a graphic designer and brewer who led the night’s ride, announced via megaphone, “Welcome to the end. We’re going to be partying all night!”

Before locking up my bike, I noticed a cluster of cyclists wearing all red, including some red wigs. They’re friends and family members who rode in honor of Steve Villarreal, a redheaded bike and skateboard enthusiast who recently passed away at age 26. His mother handed me a laminated photo of the young man grinning as he pedaled along Lake Michigan. “There’s always a lot of energy and positive people around you at Critical Mass,” Villareal’s friend Austin Johnson said. “So this was the ideal way to celebrate our friend’s life.”

As we stood by a fire at the party, Anderson offered me a sip of whiskey. Asked about the significance of the 20th anniversary ride, he contemplatively stroked his beard. He said he was impressed by the many miles of protected bike lanes that Chicago has built over the last few years, but added that he’d been a target of road rage from half a dozen motorists on his commute down Milwaukee from Logan Square to the plaza that afternoon. He was even nudged by a right-turning SUV driver who failed to yield while crossing the bike lane.

“A lot of people ask if Critical Mass is still important, and why is it even necessary anymore,” Anderson said. “But part of what the ride is about is a culture change to make bikes more visible, especially to drivers. I suspect that many folks riding on the streets of Chicago day in and day out would agree that we still have a lot of work to do.”  v

John Greenfield edits the transportation news website Streetsblog Chicago.