calendar_today 07 Nov, 2026 – 20 Mar, 2027
directions_run Running
language Official Website
sell $160.00
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:
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.
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!
Nov 07, 2026
Distance — 3.12 Miles
Type — Running
09:00
$160.00
Nov 07, 2026
Distance — 6.2 Miles
Type — Running
09:00
$160.00
Nov 07, 2026
Distance — 3.12 Miles
Type — Running
09:00
$160.00
Nov 07, 2026
Distance — 13.1 Miles
Type — Running
09:00
$160.00
Nov 07, 2026
Distance — Chilly Willy Winter Walk Series
Type — Running
09:00
$160.00
These values represent the 3-year monthly averages for November in Oconomowoc.
Learn more about the host city, Oconomowoc.
Oconomowoc is a city in Waukesha County, Wisconsin, United States. The name was derived from Coo-no-mo-wauk, the Potawatomi term for 'waterfall'. The population was 18,203 at the 2020 census. The city is partially adjacent to the Village of Lac La Belle and is near the village of Oconomowoc Lake.
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