Tom Grosspietsch was Chicago’s shepherd on wheels. His flock — the Windy City Skaters, a group that came together nearly two decades ago to share a love for rollerblading, also known as inline skating.
Mr. Grosspietsch — pronounced like Gross Peach — collected his herd of several dozen riders under the gaze of the Picasso in Daley Plaza every other Friday during the warmer months to lead its most cherished ritual: Friday Night Road Raves.
After a quick rundown of the rules — helmets were a must, and there’d be no running of red lights — he blew a whistle, and the group began rolling through the Loop with the the sounds of tunes blaring from Bluetooth speakers affixed to backpacks.
The 13-mile route was known in advance only to Mr. Grosspietsch, who created themes for each journey.
His Great Chicago Fire ride, for instance, rolled past the the site of the fire’s origin and included structures that survived the conflagration. He led a ride that went past spots associated with Democratic National Conventions and others that showcased locations seen in “Ferris Bueller’s Day Off” and “The Blues Brothers.”
His Pope Leo XIV ride went past the site of the Roman Catholic leader’s birth, the South Side ballpark of his beloved White Sox and a Portillo’s that named one of its beefs after the pontiff.
At each key spot, Mr. Grosspietsch blew his whistle, everyone stopped for a minute or two, Mr. Grosspietsch told a few interesting bits about the history connected to the spot, and then the party kept rolling.
He printed each map, which included photos and facts, handing them out after each ride.
Mr. Grosspietsch, who lived in Oak Park, died July 15 after being hospitalized in Chicago due to complications from blood cancer. He was 66.
He led his last ride last year before suffering health setbacks.
His group, which was as diverse as the waiting area for a driver’s license at a secretary of state’s office facility, traveled in the streets, prompting occasional hoots and hollers as they rolled by, say, popular nightlife strips.
Participants handed out cards to curious onlookers with information for potential recruits.
The group skated just about anywhere skates could roll — including Lower Wacker Drive and the museum campus — but stayed away from DuSable Lake Shore Drive and Michigan Avenue.
The ride was Mr. Grosspietsch’s baby.
“On every ride, he’d turn to me and say, ‘So far, so good?'” said Kirsten Lefeldt, a civil engineer who added that Mr. Grosspietsch would skate the route ahead of time for quality assurance.
Windy City Skaters is planning a memorial ride later this summer. The theme will be Mr. Grosspietsch’s life. Stops will include Grant Park, where he volunteered for years for the American Cancer Society’s Walk and Roll fundraiser; Macy’s on State Street, where Mr. Grosspietsch’s work as an art director and graphic designer was displayed in windows for many years during the holiday season; and a place along the Near South Side lakefront where his skates left an imprint in concrete that was still wet.
Mr. Grosspietsch co-founded Windy City Skaters and was the driving force behind the group, which began hosting Friday night rides in 2008.
“He touched so many lives in such a positive way,” said Nate Hill, 35, a software designer who lives in the West Loop and will help carry on Mr. Grosspietsch’s legacy by leading future rides.
“When I moved here four years ago from Indiana, I didn’t skate and was trying to figure out how to make friends,” Hill said. “I learned about the meetup, and I practiced skating and went and checked it out. And it ended up changing my life in a huge way. I met so many amazing friends. and I’ve learned so much about Chicago. Tom’s a legend in the community.”
During the Friday night rides, you’ll find Gerard Brouwer, 78, bringing up the rear, helping any stragglers and shouting “Stay the right!” to remind skaters to leave room for cars to pass.
“All of us were able to enjoy the benefits of Tom’s hard work, and there’s never been a charge or a fee for any of it,” said Brouwer, who drives two hours from his home in LaSalle County to take part in the rides.
The group includes several people from Wisconsin and transplants from European and Asian countries where inline skating is more mainstream.
“It’s a very inclusive group,” Hill said. “The only through line is people who tend to prioritize their health. And Tom got purpose from bringing the community together. That’s what he kind of lived for, in a way.”
Mr. Grosspietsch was born Aug. 6, 1959, grew up in Barrington and loved playing hockey as a kid.
He was one of 12 siblings. One of them, Joseph, has since died.
His father John Grosspietsch died 1972, and Mr. Grosspietsch stepped in, along with his siblings, to help out his mother Margo Grosspietsch, family members said.
“He was a quiet shepherd back then, too,” said Mr. Grosspietsch’s brother Mike. “He’d pile us into the family station wagon — if it was running— and drive us to a public ice rink to skate and get us out of the house and give my mom a break.”
Mr. Grosspietsch was once a competitive long-distance inline speedskater. He competed in events across the United States and Europe, mostly in his 40s.
He also hosted Skate Chicago, a free four-day event that invited skaters from around the country to take part in rides around the city.
Services have been held.