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 running series in Wisconsin that runs from November 7, 2026 to March 20, 2027. The series is produced and managed by Silver Circle Sports Events, LLC and includes events at several area venues in and around Oconomowoc, Waukesha, Menomonee Falls, Hartland and Milwaukee.
Distances and options offered in the series include:
- 5K races
- 10K races
- Half marathon at two events
- Walker division and a 2 mile walk at one event
- 5K ruck events, which are timed and have no age group awards
- Kids 1K races offered free at each Chilly Willy race
Every finisher receives a wooden finisher award called a Woodle with a magnet on the back, made from reclaimed wood. Series awards are presented to overall, age group, and team champions. To be eligible for 5K or 10K series awards, runners must participate in four of the seven races. The series uses a points system for awards with points allocated from first through tenth place, one point for finishing, division winner points, and age used as a tie breaker when needed.
Additional features noted for the series include a post-race hot chocolate bar at events, a team challenge for local teams and businesses, and an All Access Pass option that provides a reusable ankle strap for timing and bypasses packet pickup. Visit the organization's website for the most recent information.
