Howl-o-ween 5k - Dan Ryan Woods

Howl-o-ween 5k - Dan Ryan Woods takes place in Chicago, Illinois, on October 25, 2026. One distance is on offer, a 5K over 3.1 miles, starting at 9:00 a.m. at Dan Ryan Woods on the city's South Side.

Running a 5K in a forest preserve rather than on city streets usually means softer footing and fewer road crossings, so wear shoes with a little grip if recent rain has been through. The distance itself asks for sharpness rather than volume: a month of weekly 5K-pace repeats, a couple of easy days before the race, and a genuine warm-up of ten to fifteen minutes of jogging plus strides will cover it. Late October in Chicago is prime running weather, and a 3.1-mile effort is easy enough to recover from that it fits inside a build toward something longer.