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Living on the edge: The 23rd annual Chicago Perimeter Ride traced the city’s circumference in 19 hours

Riders leave Queen’s Landing during this year’s ride. At the front here are Andy and Phillip, two of the participants interviewed for this article. Photo: John Greenfield

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This post is sponsored by the Active Transportation Alliance.

This post isn't completely within Streetsblog Chicago's wheelhouse, but I thought many of our readers would enjoy it, so I recently wrote it up, mostly during an evening at my after-hours office.

I don't recall exactly when I launched the Chicago Perimeter Ride, "a century around the city," but it was around 2002. It was inspired by my then-job at the Chicagoland Bicycle Federation, now the Active Transportation Alliance, as a consultant to the Chicago Department of Transportation, arranging the installation of bike parking racks. The fieldwork required me to travel all over the city by CTA + bike, so I encountered plenty of interesting landmarks I wanted to share with others.

Elizabeth Winkowski published a travelogue of the 2006 ride for Newcity magazine in 2008. So the event is definitely at least 19 years old, and probably a few more than that.

Another writeup from Andrew Willoughby from 2012, on Streetsblog Chicago cofounder Steven Vance's and my old site Grid Chicago, says I had led the ride for the previous decade. According to Andrew, I handed off the event to my Chicago Critical Mass crony David Gebhardt that year.

Juan Dominguez, who often proposes CCM routes nowadays, also likely led the Perimeter Ride for a year or two.

Jerome Hughes is the current proprietor of the Perimeter Ride, and he says that after fixing flats on the excursion since 2015, he he started running the show about five years ago. This year's sojourn on Saturday, October 11, was supposed to depart at 9 a.m. from Buckingham Fountain on the lakefront. But that was impossible to reach because downtown streets were closed for the Chicago Marathon the next day. So we insead gathered across DuSable Lake Shore Drive at Queen's Landing. The weather was ideal: sunny in the the 70s. A couple dozen people showed up.

The 2025 ride gathers on Queen's Landing. Photo: John Greenfield

Before we started the journey, my first participation in the ride for many years, I buttonholed Jerome for a short interview. "It's a fun ride, where some people come for part of it, and some people took the whole thing, and we come back around to Buckingham Fountain, and in the middle of the night," he said. "Last year, we finished it up at around 3 a.m."

I had never ended the ride that late! "We made more stops," he explained. "We had we stopped at the Little Calumet River for an event," They also took a break to check out a show at Fitzgerald' s, a music club in west-suburban Berwyn, not far across the border.

Jerome told me this year he and his wife Jen McConnell were hosting some friends they met on RAGBRAI, [Des Moines] Register's Annual Great Bike Ride Across Iowa. "Very cool," I responded. "Well, this is sort of Chicago's answer to RAGBRAI." That would GBRAC.

"All right," I said. "Well, I'm ready to live on the edge."

"That's what we're going to do," Jerome responded. "I'm glad to have the founder with us."

Here's the route the group took, somewhere in the ballpark of 100 miles.

Image via Jerome Hughes

And here are a few shots from the beginning of the ride.

Jerome leads the group south from Queen's Landing. Photo: John Greenfield
Approaching the Adler Planetarium. Photo: John Greenfield
Promontory Point. Photo: John Geenfield

At the Point, i interviewed Phillip Pugh, who lives in Bronzeville and does media services for Northeastern Illinois University. What brought him on the trip? "My friend Tim, has been encouraging me to come on this ride for two or three years, and I finally decided to do it," Jerome said. "And the weather too. Because we don't have too many more nice days, with winter approaching, so I wanted to get in some good rides."

He said he wasn't necessarily planning on doing the whole journey. "I'm gonna ride into the afternoon, until I decide to peel off. But I just want to get in a nice, relxing long ride today. I just love riding, and I like riding with good groups of people."

Here are some photos from the next leg of the ride.

Approaching the Museum of Science and Industry. Photo: John Greenfield
Coming up on 57th Street Beach. Photo: John Greenfield
Cheri, another interviewee, and Juan Dominguez leave the South Shore Cultural Center. Photo: John Greenfield
Rainbow Beach. Photo: John Greenfield
Riding by the ore wall at Steelworkers Park. Photo: John Greenfield
Jen inside the ore wall. Photo: Aaron Conroy
The rock climbing area on the other side of the ore wall. Photo: John Greenfield

In Steelworkers Park, I had a conversation with Jeromes' friends from the Buckeye State. I'll intersperse that with photos from the next segment of the journey.

John Greenfield: You folks are visiting from Iowa City. What brought you on the ride?

Andy: Jerome told us all about this ride. It sounded great. I've never rode my bike, in Chicago before, really.

Cheri: We only knew Jerome as RAGBRAI Willie for many years. He brought his guitar and had the long braid, so he was RAGBRAI Willie [presumably a reference to Willie Nelson].

Statue of a steelworker's family in Steelworker Park. Photo: John Greenfield

Andy: With a bunch of s--- on a trailer on his bike, which he stopped doing he started realizing it wasn't the easiest thing to do. He doesn't haul as much stuff anymore.

JG: What do you think of the ride so far?

The Calumet River Bridge on 95th Street was lifted at we ate lunch at Calumet Fisheries. Photo: John Greenfield

Andy: I love it.

Cheri: Yeah, this is a great ride. This is a great day.

Riding past Halloween decorations in the East Side neighborhood.

JG: Got anything else you're planning on doing in Chicago while you're here

Andy: Specifically, I'm getting Johnnie's Beef on the way out. [Note to self: Since Johnnie's is right past the Chicago city limits at 7500 W. North Avenue, it might make a good future Perimeter Ride stop.] We've come to Chicago for weekends in the past, for Cubs games or we used to come for [Munster, IN brewery Three Floyds'] Dark Lord Days. And it would always be our Sunday tradition on the way back to get a whole bunch of Johnnie's Beef.

Johnnie's Beef in August 2018. Image: Google Maps

The thing is, the beef is really juicy, and I think it's too hot to eat right out the bag. So we roll those bags up with the beefs, and we start driving back to Iowa. By the time we get to the DeKalb Oasis, they've reached the perfect temperature, consistency, and congealed-ness."

Crossing Wolf Lake on a bike causeway in Indiana, just east of the Hoosier Curtain. Photo: John Greenfield

JG: So you're saying you get the sandwiches dipped?

Andy: Yes, as juicy as they'll give us.

Big Marsh bike park. Photo: John Greenfield

JG: Sweet or hot peppers?

Andy: Sweet and hot.

Carving at Big Marsh. Photo: John Greenfield

JG: Do you get a "combo" with Italian sausage?

Andy: I do not. Straight Italian beef. I'm gonna get, like, six of them, wrap them up, and I'll probably eat one and a half at the Oasis, and then the others will be my breakfast, lunch and dinner the next day.

Riding through Pullman National Historic Park. Photo: John Greenfield

JG: Sure, if you spend the entire previous day doing 100 miles, you've earned it.

Andy: Yes.

Stopping at a light across from the Pullman factory building. Juan helps a rider with a brake adjustment. Photo: John Greenfield

JG: Some people feel that "cheesy beefs" are not legitimate. What's your opinion on that?

Andy: Yeah, no cheese. The beef, the juice, the peppers, and the bread together is the perfect combination. You don't need anything else.

My last photo of the group that day: Riding towards the Michigan Avenue ridge in the Roseland neighborhood. Photo: John Greenfield

Once the ride got to 103rd and State streets in the Roseland community, I said farewell to the my companions, rode a mile north to the 95th/Dan Ryan Red Line station, and caught the train back north to run some errands. But here are some photos of the rest of the trip that riders shared with me to post.

Major Taylor mural at 107th and the Major Taylor Trail. Photo: Jerome Hughes
The Original Rainbow Cone in Beverly. Photo: Jerome Hughes
The tunnel in Berwyn. Photo: Jonathan Eyler-Werve
Robert and Jen at Fitzgerald's in Berwyn. Photo: Jonathan Eyler-Werve
At the legendary hotdog stand Superdawg, just before the 2 a.m. closing time. Photo: Jonathan Eyler-Werve
Jerome and Juan return to Queen's Landing at 4:30 a.m., about 19 hours after the ride departed, "a new record." Photo: Jerome Hughes.

That Sunday afternoon (after Jerome had a chance to sleep in) I texted him to ask for a final comment on the ride. "How do you do 100 miles?" he responded. "Well, you break it into little chunks."

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