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.





     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.



     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.


     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!”



     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.