Chilly Willy Winter Run Series - SEVEN Events!
Chilly Willy Winter Run Series offers seven events across Wisconsin to keep runners active through the cold season.
Race Date
Nov 7, 2026
Location
Oconomowoc, WI
Quick facts
- Date
- Saturday, November 7, 2026
- Location
- Oconomowoc, Wisconsin
- Distance
- Half marathon (13.1 mi) + 3.12 Miles, 6.2 Miles, Chilly Willy Winter Walk Series
- Course
- Loop Course
- Terrain
- Road
- USATF certified
- Not listed
Highlights
Good For
Atmosphere
Course
The Experience
The Chilly Willy Winter Run Series invites runners to embrace the Wisconsin winter across seven distinct events. Participants can choose from 5K, 10K, or half marathon distances, with a new Rucking 5K option available for those seeking a different challenge.
This series is designed to keep the competitive spirit alive and fitness levels high throughout the colder months. Runners can compete individually or as part of a team, with awards for overall, age group, and team series champions. The events are held in Oconomowoc, WI, offering a chance to experience winter running in the Midwest.
Whether you tackle one race or commit to the entire series, the Chilly Willy Winter Run Series provides a consistent opportunity to stay active and engaged with the running community during winter. The series includes a T-shirt giveaway, adding a tangible reward for participation.
Race-provided description
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.) 🚀 Skip the Lines With The CW All Access Pass! 🏃♂️ CW All Access Pass? Your ticket to skipping the packet pickup line and heading straight to the start line! How It Works: ✔ Register for the series in any distance 🏅 ✔ Opt out of a shirt and save $10 👕💰- this automatically gets you the pass ✔ Receive a reusable ankle strap for timing ⏱️ ✔ No check-in required – just show up and run! 🏃♂️🚀 More running, less waiting—because race day should be running, not the lines. 🌲 🏅 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!
Logistics
Race Day
Saturday, November 7, 2026
Start Time
9:00 AM
Giveaway
T-Shirt
Start Location
1327 Wall Street, Oconomowoc, WI, 53066
Course Info
Course Type
Loop Course
Terrain
road
Difficulty
Ultra-Flat
Net Drop/km
0 m (Flat)
Separation
0.0%
Also Offers
Quality Score
first year
no finisher counts yet
small race — neutral
needs a few years of results
3 timing sources · 3 photos
no finisher data yet
no winner time yet
typical high 55°F
Race Day Weather
5-year historical avgStart (Low)
40°
Afternoon (High)
55°
Ideal racing weather — cool and comfortable
0.1"
Precipitation
13 mph
Wind
72%
Humidity
Race Photos
Frequently asked
When is the Chilly Willy Winter Run Series - SEVEN Events!?
The Chilly Willy Winter Run Series - SEVEN Events! is held on Saturday, November 7, 2026, starting at 9:00 AM.
Where does the Chilly Willy Winter Run Series - SEVEN Events! take place?
It takes place in Oconomowoc, Wisconsin.
What distances does the Chilly Willy Winter Run Series - SEVEN Events! offer?
The half marathon (13.1 miles), plus 3.12 Miles, 6.2 Miles, Chilly Willy Winter Walk Series.
Is the Chilly Willy Winter Run Series - SEVEN Events! course flat and good for a PR?
The Chilly Willy Winter Run Series - SEVEN Events! is a ultra-flat, loop course course.
HalfRuns editorial — independent, no paid placement.
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