Inside the Chicago Courier Classic, bike messenger culture refuses to die
Jun 25, 2026
Day one I knew I’d arrived when I saw the kaleidoscope of bikes. I was greeted by Sam Crossland—a courier with long, auburn hair and a surfer’s inflection—who introduced me to a pod of messengers. Some wore Lycra, cleated cycling shoes, and helmets; others wore stylishly baggy pants and sne
akers, eschewing protection. Almost everyone was […]
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