Chilly Willy Winter Run Series
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Chilly Willy Winter Run Series 2026–27
The Chilly Willy Winter Run Series is a seven-event winter race series in Wisconsin running from November 7, 2026 to March 20, 2027. Events take place in multiple communities including Milwaukee, Oconomowoc, Waukesha, and Menomonee Falls. The series is produced and managed by Silver Circle Sports Events, LLC and lists a central location address in Oconomowoc, WI.
Distances and event types include:
- 5K
- 10K
- Half marathon
- 2-mile walk
- Kiddos 1K (free with registration)
- Ruck 5K
Series finishers receive a wooden finisher award called a Woodle, made from reclaimed wood by Ridgeway Woodworks and fitted with a magnet. A Hot Chocolate Bar will be available at each race. The series features a walker division with a request that walkers stay to the right side of the road, and a Team Challenge that encourages teams of four.
Awards and series scoring are governed by a points system. Runners must participate in at least four of the seven races to be eligible for 5K or 10K series awards. Points are allocated by place, finishers receive one point, division winners receive 11 points, and ties are broken by age with the oldest runner winning.
The CW All Access Pass allows participants who opt out of a shirt to skip packet pickup, receive a reusable ankle timing strap, and avoid check-in for races where the pass applies. Packet pickup and additional event details are provided on individual race pages. Visit the organization's website for the most recent information.
