The Way We Were: So much to observe in old photo of cycling race in Naperville

The Naperville Heritage Society could offer little information on when the photo of this bike race took place at the corner of Washington Street and Jefferson Avenue in downtown Naperville. We did, however, notice a few interesting things: it would appear the cyclists required the assistance of someone to hold up their bikes before they took off, all but two of the men in the photo are wearing hats, the man seated atop what looks like a wagon is shaded by an umbrella and some took to a rooftop to get more of a bird’s eye view of the proceedings. Among the things we do know courtesy of Naper Settlement is that bicycles became more widely available in the 1890s and Naperville’s first bike repair shop was opened in the late 1890s by Eli Stark. Women, in particular, embraced them as an easy means of transportation and fashion styles followed suit. Bulky clothing gave way to styles that were more accommodating for the female cycling and other activities.

https://www.chicagotribune.com/2025/12/19/way-we-bikes-cycling-race-naperville/

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