Howl-o-ween 5k - Dan Ryan Woods 2026

The Howl-o-ween 5k is a Halloween-themed 5k run or walk at Dan Ryan Woods in Chicago, Illinois. It is built for people who want a short fall race rather than a long-distance challenge, and the event’s dog-friendly setup fits the Howl-o-ween name. The race is held in Dan Ryan Forest Preserve, giving runners and walkers a park setting on Chicago’s South Side. It supports K9’s for Veterans, and the extras lean into the holiday mood: swag, treats, and space for participants who want to bring dogs into the day.