Chilly Willy Winter Run Series
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Chilly Willy Winter Run Series
The Chilly Willy Winter Run Series is a seven-event winter race series in Wisconsin running from November 7, 2026 to March 20, 2027. The series is produced by Silver Circle Sports Events, LLC and is based in Oconomowoc, WI at 1327 Wall Street. Individual races take place at multiple venues across the region, including Milwaukee, Oconomowoc, Waukesha, Menomonee Falls, and other local parks and trails.
Distances and event types include:
- 5K races
- 10K races
- Half marathon entries at two events
- Walk division
- Ruck 5K
- Kiddos 1K free childrens race
The series offers a CW All Access Pass for series registrants who opt out of a shirt; pass holders receive a reusable ankle strap for timing and do not need to check in for packet pickup. Every finisher receives a wooden finisher medal called a Woodle, made from reclaimed wood with a magnet on the back.
Awards are presented to overall, age group, and team series champions. To be eligible for final series awards runners must participate in at least four of the seven races. Series scoring uses a points system for placements, with division winners allocated bonus points and age used as a tiebreaker when needed.
Walkers are welcome and asked to keep to the right side of the course. The series does not offer refunds but allows referrals, transfers, deferrals, shirt size changes, and distance changes. Visit the organization's website for the most recent information.
