Draped in multicolor string lights and blasting Christmas music, a group of over 20 skaters weaved through the streets of Chicago on a recent night to celebrate the holiday season.
The group’s leader, 65-year-old Tom Grosspietsch, said he hoped that the skate would “lift up spirits” across the city in time for the holiday season, with the route intentionally passing through heavily populated areas with restaurants and nightlife.
“It’s like the circus is coming to town, and everybody honks their horns and yells and cheers from the outdoor bars,” Grosspietsch said.
Skating approximately 12 miles along city streets during regular Friday night “Road Raves,” the Windy City Skaters have been putting their wheels to the pavement for over a decade. Their themed skates often highlight Chicago history and take participants from neighborhood to neighborhood to visit little-known landmarks, with past subjects including Malört, cicadas, punk rock and the Chicago sewer system.
The group of recreational skaters has been convening since 2008, using social media platforms such as Facebook and Meetup.com to spread the word about the skates, which typically take place every other week from May through October. Their Facebook group has over 3,400 members.
“We have a very diverse skating crowd, by age, by race, by backgrounds, by careers, by jobs,” said Mary Meixner, a Chicago attorney who regularly participates in the Road Raves. “But in the end, we’re all skating friends. We just want to skate. And I think that’s what’s really cool, on these adventurous Friday night skates.”
Meixner’s father owned a skating rink in Minnesota for over 47 years, she said. She “grew up skating,” rollerblading for fun in addition to competing as a figure skater in her teenage years.
After she moved to Chicago in 2001, she continued to rollerblade alone on the city’s trails until she found Windy City Skaters approximately five years ago.
In addition to the community, Meixner said that Windy City Skaters routes are “actually educational,” as she is “learning about the city and skating to neighborhoods and communities that I would otherwise have no reason or incentive to go to,” she said.
Grosspietsch, who chooses the themes for each skate, studies up on Chicago history in order to plan his routes, which he then skates alone at least once as a trial run.
Over the years, the group has held skates centered around the Great Chicago Fire, the Rolling Stones, labor unions and classic Chicago movies like “The Blues Brothers” and “Ferris Bueller’s Day Off.”
The themes are often “topical,” Grosspietsch said, reflecting current events and news stories. He held a Road Rave centered around the history of Chicago political conventions during the DNC and a music festival-themed skate during Riot Fest.
As broods of cicadas emerged this summer, Grosspietsch organized a skate that took participants past insect-themed exhibitions at the Peggy Notebaert Nature Museum and the Field Museum, a cicada-free zone at Navy Pier and a cafe that served deep-fried cicadas during another wave of the insects in 1990.
He has also led a Jeppson’s Malört-themed skate centered around Chicago’s iconic liqueur, for which the stops included the Malört distillery, many of Chicago’s top Malört bars and the beverage’s Near North Side birthplace.
Windy City Skaters also holds a free, multiday street skating event in September called Skate Chicago, with daily themed skates of up to 20 miles. One of the skates this year focused on the Chicago-based history of “The Wizard of Oz,” stopping by sites including author L. Frank Baum’s former Humboldt Park home and the city’s own Oz Park.
Skaters from all around the nation “descend on Chicago” for the event, said Windy City Skaters regular John Price. One of this year’s skates attracted around 200 people, he said, with around “47 people from Miami alone.”
Price, 57, lives in Milwaukee and drives down to Chicago every other week to participate in the Road Raves. He has only missed one skate in the past three years — and that was because his car broke down, he said.
“The first time I went with Windy City Skaters on a Road Rave, we went on the 606 and at one point a lace of mine, the loop of the lace, got around my wheel and threw me down to the ground, putting a hole in my jeans and like a big scab on my knee,” Price said. “These guys are hardcore … I kind of got hooked right then.”
Dawn Cooley, a minister who moved from Chicago to Minneapolis last year, has already begun trying to “start something similar” to Windy City Skaters in her new city.
“I loved everything,” Cooley said. “As somebody who was new to Chicagoland, it was an amazing way to get to see the city in a way that I never would have gotten to … And skating around Chicago, especially at night, when the sun has set, is just the most magical thing.”
Windy City Skaters is a “third place on wheels,” Cooley said. During the Road Raves, she said, it was “so easy to skate with somebody and have a great conversation for 10 minutes, then they go ahead at the intersection, and you find yourself talking to somebody else.”
Lasting between two-and-a-half to three hours on average, Road Raves weave through a network of bike lanes and side streets, with brief stops at the key sites connected to the theme of the day’s route, Grosspietsch said.
They make sure to “keep the group together,” Grosspietsch said, never stretching out across more than two or three blocks and stopping to let any stragglers catch up.
“It’s not a race,” Grosspietsch said. “Nobody wins. There are no medals, there’s no glory, no podiums, no money.”
The Road Raves’ ground rules include stopping at red lights and remaining either within a bike lane or one lane of traffic, Grosspietsch said. Although most of the participants are inline skaters, bikers and skateboarders are also welcome, with the skates usually attracting between 30 to 60 people.
Chicago has a rich skating community, those interviewed said, with groups dedicated to roller derby, rink skating, speed skating, ice skating and “JB Skating,” a dance-like style that originated on Chicago’s South Side and is typically done to soul or funk music.
Nate Hill, a 33-year-old who runs his own software company, became interested in skating after joining Windy City Skaters over two years ago and said it is now “one of (his) favorite things.” He now organizes group skates during Windy City Skaters’ winter off-season, and has started a Reddit page to inspire a “common link” between Chicago’s various skating subcultures and spread the word about new skating events.
“One of my goals is to try to connect skaters in different communities,” Hill said. “I am really thankful for what Tom (Grosspietsch) does, because that got me into skating. If I could sort of pay it forward and try to do the same for other people, that’d be worthwhile.”
One of Windy City Skaters’ Road Raves, which they repeated twice this year, focuses on the history of roller skating in Chicago. Stops along the way include the restaurant where promoter Leo A. Seltzer drew up the plan for the sport of roller derby, the former homes of defunct roller rinks, roller skate factories and the Montgomery Ward mail-order warehouse where employees traversed the large space wearing skates.
Grosspietsch, who has been inline skating for 30 years, noted that Chicago was a great city to skate in given its bike lanes and flat landscape. Rather than going around in circles indoors, he said, “with inline skates, the whole world is your skate rink.”
He said that his ultimate goal with Windy City Skaters is “building community.”
“We are sort of outcasts, a little bit,” Grosspietsch said. “We are skaters in a walker, runner, biker, car world … So we’re inclusive, we let anybody skate with us. That’s why we let them. We wait for the slower skaters in the back to catch up. We don’t leave anybody out there. We don’t ditch anybody.”