Chilly Willy Winter Run Series

MAR
14
2026
This winter series features seven races from November to March across Wisconsin. Runners can choose from 5K, 10K, half marathon, walk, or ruck events. All finishers get a unique wooden medal, and a hot chocolate bar awaits at the finish.
Sat 14 Mar 2026
Half Marathon 10 kilometers 5 kilometers

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Event Overview

The Chilly Willy Winter Run Series consists of seven individual races held in Wisconsin from November 2025 to March 2026. The events take place at various locations in Oconomowoc, Waukesha, Hartland, and Menomonee Falls.

Event Distances

Participants can choose from several activities across the series. The offered distances vary per individual race event.

  • 5K and 10K options at most events.
  • Two half marathon distances are included in the series.
  • A walking division is available.
  • A new 5K ruck event, involving walking with a weighted backpack.

Additional Information

Finishers receive a unique wooden medal, referred to as a "Woodle," made from reclaimed wood. A post-race hot chocolate bar with toppings is available at each event. Awards are given for overall, age group, and team series champions, with special "Average Joe & Jane Awards" for the middle-finishing male and female runners in the 5K races. A team challenge encourages groups of four to participate.

The series registration operates as an "All Access Pass," allowing entry to all events. For certain individual races, registration for single events may open later. Children's 1K races are free. T-shirts are available for series registrants, subject to a deadline. Visit the organization's website for the most recent information.

Half Marathon
Chilly Willy Winter Run Series Half
10 km
Chilly Willy Winter Run Series 10k
5 km
Chilly Willy Winter Ruck Series 5k
5 km
Chilly Willy Winter Run Series 5k
5 km
Chilly Willy Winter Walk Series 5k