Chilly Willy Winter Run Series

MAR
22
2026
Test your mettle across seven winter events in Wisconsin featuring running, walking, and rucking. Enjoy a post race hot chocolate bar and earn unique wooden medals while competing for series championship awards.
Sun 22 Mar 2026
Half Marathon 10 kilometers 5 kilometers

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Event Overview

The Chilly Willy Winter Run Series is a multi-event sports series held in Wisconsin between November 2025 and March 2026. Organized by Silver Circle Sports Events, LLC, the series spans seven different dates at various locations including Oconomowoc, Milwaukee, Waukesha, and Menomonee Park. The series features multiple disciplines including running, walking, and rucking.

Participation Options

The series offers several distance categories to accommodate different activities. Participants can choose from the following event types:

  • 5K Run
  • 10K Run
  • Half Marathon
  • 5K Walk
  • 5K Ruck
  • Kiddo's 1K

The rucking category involves walking or hiking with a weighted backpack. While rucking events are timed, they do not include age group awards. For the running events, participants who select the half marathon option are automatically entered into the 10K category for dates where the longer distance is not offered. Similarly, 10K runners are moved to the 5K for events without a 10K option. Free 1K races are available for children at all series events.

Series Awards and Scoring

A points system determines the overall champions for the series. Points are awarded based on finishing rank, with 10 points for first place down to 1 point for 10th place; all finishers receive at least one point. To be eligible for final championship awards and trophies, participants must complete at least four of the seven races in the same distance category. Overall, age group, and team awards are presented at a wrap-up event following the final race in March.

Amenities and Features

Each finisher receives a "Woodle," a magnetic medal handcrafted from reclaimed wood. A hot chocolate bar with various toppings is provided at the finish line of every event. Participants also have the option of an "All Access Pass," which utilizes a reusable ankle strap for timing and allows runners to bypass standard check-in lines on race days. 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
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