I was out in the burbs this past weekend to do a few things and visit with some family, and I decided to go for a quick cruise through the woods on the DesPlaines River Trail. All of the park entrances were closed off and blockaded with mounds of snow (Apparently people out here don't do things outdoors in the winter), and so after some searching, I was able to sneak in by parking my car in a hotel parking lot that provided easy access to the trail.
It was relatively warm, compared to the recent deep freeze that hit Chicago, delivering the coldest temps in THE HISTORY OF CHICAGO with lows hitting -15. I wore no cycling-specific clothing on this ride, only a moisture-wicking T-shirt, a hoody, and a coat, with denim jeans, a hat, gloves, and heavy wool socks with leather boots. When those boots are paired with the heavy wool, they are far warmer than any cycling shoe/bootie combination I've ever tried (plus I can wear them every day while off the bike too. That's a good investment in my mind). With that setup, I was beyond warm. I was actually sweating. That may be partially attributed to the fact that most of the ride was pretty strenuous. Just trying to stay on the bike was a challenge. The trail was so deep with snow that my rear tire was often spinning out and my front wheel was constantly washing out, causing me to frequently put a foot down. It was a bit frustrating and I ended up doing more hiking than cycling, but it was still nice to be out in the woods watching the snow fall.
I'm guessing this terrain would have been better suited for a fatbike than my steel 29'er, but what can you do. I was reminiscing of the Great Western Trail that I used to ride during the winter in DeKalb, where the "slednecks" would pack the trail down so hard with their motor vehicles that it could be easily ridden with a cross bike at times. There were very few tracks on this trail, aside from some footprints. It's a bit sad to see so few people able to take advantage of this great resource.

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