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Exploring this historic Pullman railcar factory on the Far South Side. All photos by Andrew Bedno.

For the past decade John has led the Chicago Perimeter Ride, a roughly hundred-mile pedal around the approximate edge of the city, visiting historic sites and wacky commercial architecture. This year he handed over the reins to David Gebhardt, who did an excellent job planning and leading the ride, with dozens of people participating over the course of the long day. Andrew Willoughby, a car-free Chicagoan who moved here from Oklahoma two years ago for “the music, architecture and freedom to ride a bike everywhere,” provided the following write-up. Andrew tweets at @willowbeehive.

I had no idea what to expect. I’ll admit, I was a bit nervous. Biking a hundred miles in a day did not seem like an easy thing to do. There was a reason I had never attempted it before: I’m not a professional, I just bike to work every day and around town. Yet, there I was, watching Buckingham Fountain thrust its first drops of water into the air as I waited with fifty other riders, many who were attempting their first century too.

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Start of the ride at Buckingham Fountain.

I stumbled across the Perimeter Ride through The Derailleur, an unofficial publication of Chicago Critical Mass. The ride is one hundred miles along the edge of the city, ridden mass-style at a reasonable pace, and no rider is left behind. John Greenfield revealed the secret to riding a century when he first led the ride in 2002. The trick is to just show up, make new friends, and enjoy the ride.

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David Gebhart, our fearless leader, arrived with oatmeal cookies and shared them with folks. Then we saddled up and began our ride, heading south down the Lakefront Trail, stopping briefly to discuss group riding safety and select our outstanding sweep, Oboi Reed. In reality, we spent more time on our feet than in the saddle. It wasn’t a race; we had all day, and we had great plans.

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We took a water break and marveled the South Shore Cultural Center’s beautiful solarium, snacked on smoked trout from Calumet Fisheries while waiting for the 95th Street “Blues Brothers” drawbridge to lower. We took a few laps around the velodrome at the Lakeside Velo Works, toured through the historic Pullman factory, picked hops and enjoyed ale at Argus Brewery, and had the best ice-cream and malt ever at Original rainbow Cone.

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Lakeside Velo Works.

We picked up a random kid in Berwyn who was out for a ride and decided to join us all the way to the end, cruised by the giant red Radio Flyer wagon, rode the moonlit North Branch Trail, visited the Leaning Tower of Niles and, best of all, crashed a block party.

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Superdawg, Devon and Milwaukee.

Our shouts of “Happy Saturday!” turned into “Happy Sunday!” and after sixteen hours, we arrived back at Buckingham Fountain. Our group had dwindled to thirteen riders and the Loop seemed unrecognizable and foreign, as if we had been gone for months. “We just rode a-hundred miles!” we bellowed before celebratory whiskey shots at Miller’s Pub. We can tell our family and friends about the places we saw and how far we rode, but the true gems are hard to describe. You just have to experience the Perimeter Ride for yourself. And that’s the greatest thing about it- you totally can.

See more of Andrew’s Perimeter Ride photos here.