Credit: John Greenfield

Some people probably think of me as the Perimeter King of Chicago. Along with many other trips involving cycling the outer edge of places—Illinois, Lake Michigan, three-quarters of the continental U.S.—for the better part of a decade I led the annual Chicago Perimeter Ride. That event typically drew about 100 people for a leisurely all-day-and-evening pedal around the city.

But I’ve suffered from imposter syndrome. While the Perimeter Ride was always a blast, it was actually a very streamlined route that came nowhere close to tracing the actual complex, zigzagging city limits.

So for years I’ve been meaning to make things right by biking the exact border of Chicago, or as close as possible without risking being flattened by a semi driver. The COVID quarantine, when entertainment options are limited, seemed like an ideal time to do it. I planned to spread out the trip over two days, spending a night away from home, so I’d basically be taking a vacation solely within the city limits.

I ruled out pedaling around O’Hare, since that would involve miles on a nightmarish seven-lane stretch of Touhy. I also decided not to bother tracing the outlines of Norridge and Harwood Heights, those suburbs that are oddly embedded within Chicago’s northwest side for long-forgotten political reasons. And where the border is a busy main street, and there’s a chill, leafy residential road parallel to it nearby, I’d take that instead, to ensure my journey was more joyride than hellride, as the late Wesley Willis would say.

Around noon on a 91-degree August Saturday, I start my 116-mile trip on the Lakefront Trail at Montrose, with a counterclockwise route planned for optimal shoreline views. Pedaling east toward the park path that hugs crescent-shaped Montrose Beach, I’m annoyed to see that, although the local beach bar is open and bustling, lifeguards are still shooing beachgoers off the sand as part of Mayor Lightfoot’s dubious pandemic shoreline safety strategy. The following Saturday someone will nearly drown while swimming off the unsupervised rocky revetment just north of the beach.

Loyola Beach, seen through Lynn Takata’s “Waveform” sculpture at Pratt Boulevard
Loyola Beach, seen through Lynn Takata’s “Waveform” sculpture at Pratt BoulevardCredit: John Greenfield

After tagging the Evanston border in Rogers Park, the northeast corner of the city, I pedal west down Howard into West Ridge, stopping to pick up a fried clam lunch at the old-school Fish Keg storefront. Rolling south on Kedzie, I’m passing by the center of Chicago’s Orthodox Jewish community. A preteen girl and boy walk down the street, the latter in suit, fedora, and sidelocks.

Continuing west on busy Devon, I pass Novelty Golf & Games on the Lincolnwood side. The course includes a giant rooster, a miniature Hancock Tower, and an ersatz Easter Island moai.

Just west of the Edens, I follow the borderline on Ionia into pleasantly sedate Edgebrook. As I round a northerly knob of the city, the suburb-in-the-city feel is hammered home by the sight of an older gentleman watering the yard of his ranch house while sitting in the driveway on a striped lawn chair that mirrors the home’s American flag.

The Leaning Tower of Niles
The Leaning Tower of NilesCredit: John Greenfield

Rolling west on Touhy, I pass the Leaning Tower of Niles, a half-size replica of the Pisa landmark. Across the street is the Edgebrook Motel, with an appealingly garish red and seafoam-green sign, the first of several examples of retro-futurist “Googie” architecture I’ll encounter on this trek.

A mile on the North Branch Trail takes me to one of Chicagoland’s best-known examples of Googie, Superdawg Drive-In. Its midcentury design features blue and white diamond panels, red neon, and winking anthropomorphic wieners on the roof.

Soon I’m tracing the outline of Edison Park, Chicago’s northwestern-most neighborhood. Eighty-seven percent white, it’s popular with Chicago city workers, many of whom might prefer to live in the suburbs, but need to meet the city’s residency requirement. Ebinger Elementary displays a “We Support Our First Responders” banner with images of a firefighter and a cop.

After rolling southwest, I enjoy several miles of serene riding on the wooded Des Plaines River Trail. Exiting the path at Belmont, I resist the temptation to detour to River Grove to visit Gene & Jude’s, famous for its minimalist “depression dogs” (onion, relish, mustard, and sport peppers only), and Hala Kahiki, the historic multiroom tiki complex next door.

Heading east I’m in Dunning, where I pass Truc Lam Temple, a Vietnamese house of worship that recently relocated from Uptown. A plump, grinning Buddha statue reclines in front.

Pedaling into Austin, I pass Ben’s Bar-Be-Cue, in a beautiful old terra-cotta storefront. Continuing south on Mason and Mayfield as the sun descends, I spot many “Black Lives Matter” signs and tricolor Black Liberation flags on display. Kids are playing on the sidewalk with toy cars and scooters, or jumping on a trampoline next to a community garden. People sell sno-balls with vividly colored syrups from card tables. Five swan-shaped planters stand cheerfully on a brick stoop. As I cross Madison, I look left toward Loop skyscrapers tinted pink by the sunset, about seven miles east, but seemingly a world away.

SuperdawgCredit: John Greenfield

After crossing Columbus Park and rolling southeast through an industrial zone, I’m at 26th in Little Village, Chicago’s second-busiest retail strip, where it’s definitely time for dinner. At Taqueria Los Gallos, I pick up a tub of their specialty, carne en su jugo: beef, bacon, and beans in broth, garnished with radishes, avocado, and lime. I feast at nearby Manuel Perez Jr. Plaza. Across the street, a raucous band featuring tumbling timbale rhythms and a prominent tuba blares from a backyard party. Someone sets off fireworks and the ground shakes.

Refueled, I continue south on the Pulaski Bridge over the Chicago Sanitary and Ship Canal into Brighton Park, then take residential streets west through Garfield Ridge, part of the southwest side bungalow belt. There are many backyard gatherings here, including a full-blown house music dance party in someone’s garage.

I’m sleeping at the iconic Rainbow Motel, known for its waterbed-and-Jacuzzi rooms, including ones with Las Vegas, Hawaiian, outer space, and, oddly, sandwich themes. While I feel a little silly staying at a love hotel solo, I spent a night there with a girlfriend years ago, so I know it’s a reasonably sanitary, non-scary place. It’s also the cheapest option in the area, save for the nearby Skylark Motel which, ominously, doesn’t offer overnight stays until after midnight. Granted, my bare-bones single room is nothing to write home about, and when I ask the desk clerk if it comes with a complimentary bottle of spumante like last time, he just laughs at me.

In the morning, after grabbing a Danish and doughnut across the street at busy Weber’s Bakery, I pedal east on 64th in the Clearing neighborhood. I’m once again in cop-and-fireman land, as evidenced by the many variations on Blue Lives Matter flags flying, including one that includes a red stripe for firefighters and a green one for border patrol agents.

Rolling southeast into Ashburn, I check out Vito & Nick’s, a contender for the best thin crust in Chicago, then head to Lawndale and Columbus to visit the shrine and mural honoring Issac Martinez, 13. An allegedly intoxicated hit-and-run driver killed Martinez on his bike last June. A white-painted “ghost bike” was also installed at the crash site with a sign reading “Safe Bike Lanes!”

Pedaling east into Beverly, I grab a snack of chili cheese fries at Janson’s Drive-In, which has another awesome Googie sign, serenaded by Buddy Holly and Chubby Checker. From there, annoyingly, the city boundaries veer west again, taking me farther from my finish line.

Crossing Sacramento, I’m in Mount Greenwood, at the southwest corner of the city. It’s another overwhelmingly white city worker neighborhood, with a history of racial tension. After rounding Saint Xavier University, I pass a house with a “Don’t Tread on Me” flag, a reminder that I’m in the only part of Chicago that went for Trump in 2016.

I ride three sides of Saint Casimir Catholic Cemetery on hectic multilane roads, passing yet another cool Googie sign, at Fox Home Center in Alsip. Returning east to Morgan Park, I notice St. Walter Catholic Church has an outdoor display of small sculptures of Jesus walking the Stations of the Cross. Sadly, someone has pried one of the metal crucifixes from his hands.

I consider veering a mile north to Home of the Hoagy to sample a sweet steak, the legendary south-side-only cheesesteak variant, but decide I need to stay focused on my task.

View from the Indiana Avenue bridge over the Calumet River
View from the Indiana Avenue bridge over the Calumet RiverCredit: John Greenfield

Continuing southeast into West Pullman, the 12700 block of South Morgan has a block club sign prohibiting activities ranging from ball playing to drug dealing. This corner of the neighborhood seems neat and orderly. Tidy homes on 129th back up to the Calumet River.

On the other side of the river in the tiny Riverdale enclave, the only Chicago neighborhood south of the Calumet, it’s a different story. Many houses are falling apart, seemingly awaiting demolition. Local community advocate Fatimah Al-Nurridin will later tell me she’s not sure why this is the case, but there’s interest in improving the area.

After I head northeast into the Altgeld Gardens housing project, two young boys on a gas-powered dirt bike try to talk me into racing them for a $5 bet so they can buy Cokes. “Sorry guys, I’ve got to keep moving,” I mumble through my mask. If I was quicker on my feet, I’d ask if they know Deloris Lucas, known as “The Bike Lady” because she runs the cycling and wellness group We Keep You Rollin’ out of the Golden Gate neighborhood, next door to Altgeld.

Next I make the harrowing but basically unavoidable trip east on high-speed 130th to get to Hegewisch, at the southeast corner of the city. The neighborhood feels like a sleepy small town in Indiana, which lies just east. I grab a plump chicken-filled masa pocket at Gorditas Adrian’s, then roll east to tag the Hoosier border, passing Harbor Point Estates, Chicago’s only trailer park.

Finally it’s time to return north. After rolling by Club 81 Too, a longtime corner bar known for its Friday fish fries, I skirt Wolf Lake, which straddles the Illinois-Indiana border and was home to an active Nike missile silo during the Cold War. Then I pick up the Burnham Greenway and ride through lakeside Calumet Park, full of people grilling.

Calumet Fisheries
Calumet FisheriesCredit: John Greenfield

Pedaling west on 95th, I stop at Calumet Fisheries for a gorgeous hunk of garlic-pepper smoked salmon. The seafood shack stands next to the river bridge Jake and Elwood famously jumped in the Bluesmobile.

Soon I’m at the Lakefront Trail again. I’ve got 16 miles of what should be smooth sailing on familiar turf with a sweet tailwind to complete my circuit.

But suddenly the sky darkens, and the wind does a 180. By the time I reach Promontory Point, I’m fighting a headwind and downpour, rolling into the jaws of a thunderstorm. Weirdly, the setting sun remains visible to my left, and then a rainbow materializes over Lake Michigan.

Luckily, the storm soon dissipates, and my spin back to Montrose is uneventful. But I can’t imagine a more fitting grand finale to my epic circuit around Chicago than that bizarro sunset-thunder-rainbow.  v