Chilly Willy Winter Run Series - SEVEN Events!

Sat, Nov 7, 2026, 9:00 AM CST

Location: Oconomowoc, WI; 1327 Wall Street, The Greatest Place on Earth - WISCONSIN!, 53066
Type: RUN

At a glance

Bundle up and lace up for the Chilly Willy Winter Run Series, where hot competition meets the frost across seven unique events, including rucking.

Fun
Competitive
Quirky

Great for

Military & First Responders

Embrace the chill with the Chilly Willy Winter Run Series, a beloved collection of seven events designed to keep you active all season. Presented by Silver Circle Sports Events, this series invites runners to experience Wisconsin winter at its best. Expect hot competition across various distances, including 5K, 10K, and two half marathons. New this year, explore rucking, a unique weighted backpack activity, available at all events. Whether you run one or all, prepare for a blast and a chance to earn series champion awards.

What to expect

Runners can choose from 5K, 10K, and half marathon distances across the series.
Experience the new rucking option, a timed 5K with a weighted backpack.
Compete for overall, age group, and team series champion awards.

Standout details

Seven-event winter series
Includes 5K, 10K, and half marathon
New rucking option (5K with weighted pack)
Awards for series champions

Perks & features

Awards

From the public listing — confirm on the official site.

Auto-drafted from the public listing — confirm details on the official event page before signing up.

Distances & registration

5 options

Registration for all distances is through the official signup link above.

3.12 Miles
Sat, Nov 7, 9:00 AM CST · From $173.30
Opens Mar 22, 2026, 1:00 AM CDT · Closes Nov 8, 2026, 6:59 PM CST
3.12 Miles
Sat, Nov 7, 9:00 AM CST · From $173.30
Opens Mar 21, 2026, 8:00 PM CDT · Closes Nov 8, 2026, 6:59 PM CST
6.2 Miles
Sat, Nov 7, 9:00 AM CST · From $130.10
Opens Mar 22, 2026, 1:00 AM CDT · Closes Dec 9, 2026, 6:59 PM CST

+ 2 more options

13.1 Miles
Sat, Nov 7, 9:00 AM CST · From $173.30
Opens Mar 22, 2026, 1:00 AM CDT · Closes Nov 8, 2026, 6:59 PM CST
Chilly Willy Winter Walk Series
Sat, Nov 7, 9:00 AM CST · From $173.30
Opens Mar 21, 2026, 1:00 AM CDT · Closes Nov 8, 2026, 6:59 PM CST

Vibe Check

Steady Effort

longer distance

The course

Flat
Timed race

From the organizer

2026–27 Wisconsin Chilly Willy Winter Run Series❄️🏃‍♂️🏃‍♀️

Presented by Silver Circle Sports Events, LLC

Bundle up and lace up— Old Man Winter is ready to race ! ❄️ Join us for the 2026–27 Wisconsin Chilly Willy Winter Run Series , where chilly temps meet hot competition across seven exciting events. This beloved winter series is your chance to embrace the frost, stay active all season, and have a blast doing it!

Whether you're racing solo or forming a team, there's a distance for everyone:

5K and 10K options at most events

Two half marathons included in the series (Participants who choose the half marathon option will be automatically entered into the 10K category for events that do not offer the half distance.) New This Year: Rucking! We're excited to introduce Rucking to all Chilly Willy Winter Series events! Rucking is a fitness activity that combines walking or hiking with a weighted backpack—also known as a rucksack. Originating from military training, rucking has become a popular, low-impact workout for people of all fitness levels.

Ready to give it a try? Load up your pack and take on a 5K ruck at any of our events.

Please note: Rucking events are timed, but there are no age group awards.

🏅 Awards will be presented to overall, age group, and team series champions. Don’t miss your chance to experience Wisconsin winter running at its best . Run one race—or run them all. Either way, we’ll see you at the start line!

Ready to run? Register now!

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