Chilly Willy Winter Run Series - SEVEN Events!
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!
🏅 Awards will be presented to overall, age group, and team series champions.
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!
Pick your distance
Running
Chilly Willy Winter Run Series 5K
Chilly Willy Winter Run Series 10K
Chilly Willy Winter Run Series Half
Series runners who select the half marathon option will be automatically dropped to the 10K distance for races that do not have a half marathon distance.
Chilly Willy Winter Ruck Series 5K
Typical race-day weather
Based on 11 years of Open-Meteo archive data for this event's race dates in Oconomowoc, plus the 3 days either side.
The sun rises at 6:36 AM and sets at 4:38 PM local time (CST) in Oconomowoc on November 7, 2026 — 10h 01m of daylight.
Course
No course map published yet.
The organizer hasn't released a route for this event, and we don't publish guesses. If you're the organizer, send us a GPX file and we'll draw the profile.
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Other races near Oconomowoc
Different organizers, within 40 miles, in the next three months
OconoWattaWoc
Zachariah's Acres Fall Run, Walk & Roll
OPEF Trick or Trot
Run Like a Rubber Clucker
🏃 Plan Your Next Race in Oconomowoc
Find upcoming events by distance:
- Oconomowoc 5K Races 18 races
- 10K Run Events in Oconomowoc 9 races
- Oconomowoc Half Marathons 8 races
- Marathons in Oconomowoc 2 races
- Oconomowoc Running Calendar 2026 20 races
Where this page comes from. Race details were last updated on . We re-check listings regularly and again in the week before race day.
- Entries, prices, waves and inclusions — the event's official registration page
- Temperature and humidity — Copernicus ERA5 reanalysis via Open-Meteo (CC BY 4.0)
- Elevation and terrain relief — Copernicus DEM GLO-90, ESA (CC BY 4.0)
- Comparisons and counts — Race Discovery calendar, 23 Oconomowoc events
Spotted something wrong? Tell us and we'll fix it.