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Chilly Willy Winter Run Series - SEVEN Events!
Half Marathon10K5K1KRegistration open

Chilly Willy Winter Run Series - SEVEN Events!

Oconomowoc, Wisconsin250 spots
Entry from
$225
Days to go
32
Register from $225 on RunSignUprunsignup.com

At a glance

Date
Nov 7, 2026 – Mar 20, 2027
Location
Oconomowoc, Wisconsin
Distances
Half Marathon, 10K, 5K, 1K
Registration
Registration open until Dec 10, 2026, via runsignup.com
Official site
runsignup.com
Listed from
RunSignUp
Last checked
Sep 28, 2026

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About this race

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!

Key dates

Tier 2 ends

Jun 28, 2025

Tier 3 ends

Jul 29, 2025

Tier 4 ends

Aug 29, 2025

Tier 5 ends

Sep 28, 2025

Tier 6 ends

Oct 29, 2025

Tier 7 ends

Nov 8, 2025

Tier 8 ends

Nov 10, 2025

Tier 8 ends

Dec 11, 2025

Tier 1 ends

Mar 24, 2026

Tier 2 ends

Jun 27, 2026

Tier 3 ends

Jul 28, 2026

Tier 4 ends

Aug 28, 2026

Tier 5 ends

Sep 27, 2026

Tier 6 ends

Oct 28, 2026

22d

Race day

Nov 7, 2026

32d

Tier 7 ends

Nov 7, 2026

32d

Tier 8 ends

Nov 9, 2026

34d

Registration closes

Dec 10, 2026

65d

Tier 8 ends

Dec 10, 2026

65d

Pricing

Chilly Willy Winter Ruck Series 5K

Tier 6, then $235 from Oct 28, 2026

$225

Chilly Willy Winter Run Series 10K

Tier 6, then $235 from Oct 28, 2026

$225

Chilly Willy Winter Run Series 5K

Tier 6, then $235 from Oct 28, 2026

$225

Chilly Willy Winter Run Series Half

Tier 6, then $235 from Oct 28, 2026

$225

Chilly Willy Winter Walk Series

Tier 6, then $235 from Oct 28, 2026

$225

5K

Tier 7 ended Dec 6, 2017

See registration

Chilly Winter Winter Run Series 10K

Tier 4 ended Dec 1, 2020

See registration

Chilly Winter Winter Run Series 5K

Tier 4 ended Dec 1, 2020

See registration

Chilly Winter Winter Run Series Half

Tier 4 ended Dec 1, 2020

See registration

Kiddo's 1K

Standard ended Nov 23, 2023

See registration

Series Registration

Tier 6 ended Nov 28, 2018

See registration

Virtual Any Distance

Standard ended Nov 7, 2020

See registration

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Tune-up races

Straight-line distance

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    Also a half marathon, 5 mi from Chilly Willy Winter Run Series - SEVEN Events!, registration open

Straight-line distance

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