I thought some people may be interested in this article which appears as part of a larger online encyclopedia (which I had a part in creating...), explaining the history of bicycling. It is focused on how bicycling developed in Chicago, but still looks at the larger picture. Anyway, thought it might be of interest...

Bicycling entry from the Encyclopedia of Chicago

All of the images are "zoomable". Click on the thumbnail of the Lakeview Cycling Club, and zoom in to see their bikes.

I heard that there was a lot of bicycle racing in Sherman Park in Chicago when it was first built afer the turn of the century (last one, not this one), however I've not been able to confirm it. Anyway, I raced USCF a couple of times there in the late 1980s and was told that the course we raced on was a popular one in the early 1900s.