Chilly Willy Winter Run Series - SEVEN Events! 2026
- Date
- Saturday, November 7, 2026
- Start time
- 9:00 AM start (Chicago)
- Location
- Oconomowoc, Wisconsin
- Entry fee
- From $215
- Included with entry
- Includes a shirt
- Fundraising
- Takes optional donations when you register
Registration is open.
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Events and entry fees
| Event | Distance | When | Entry fee | Cap |
|---|---|---|---|---|
| Chilly Willy Winter Ruck Series 5K | 5K | Nov 7, 20269:00 AM | $215$225 after Sep 27, 2026 | – |
| Chilly Willy Winter Run Series 10K | 10K | Nov 7, 20269:00 AM | $215$225 after Sep 27, 2026 | – |
| Chilly Willy Winter Run Series 5K | 5K | Nov 7, 20269:00 AM | $215$225 after Sep 27, 2026 | – |
| Chilly Willy Winter Run Series Half | Half Marathon | Nov 7, 20269:00 AM | $215$225 after Sep 27, 2026 | – |
| Chilly Willy Winter Walk Series | – | Nov 7, 20269:00 AM | $215$225 after Sep 27, 2026 | – |
Entry fees exclude processing fees. Prices and dates come from the race's registration page and refresh nightly.
Race day planning
Entry fee schedule
- Chilly Willy Winter Ruck Series 5K and Chilly Willy Winter Run Series 5K and Chilly Willy Winter Run Series Half and Chilly Willy Winter Walk Series: $225 until Oct 28, then $235 until Nov 7, then $220 until Nov 9.
- Chilly Willy Winter Run Series 10K: $225 until Oct 28, then $235 until Nov 7, then $220 until Dec 10.
Online registration closes Dec 10, 2026, unless the race fills first.
How the price compares
At $215, entry is about 231 percent above a typical half marathon in Wisconsin, which costs $65 right now.
What a typical finish looks like
A typical finisher at a half marathon in Oconomowoc runs 2:04:35, about 9:30 a mile, based on 5 races with published results. Women typically finish in 2:11:12 and men in 1:53:51.
Light and altitude
Sunrise on race morning is at about 6:35 AM, and the Chilly Willy Winter Ruck Series 5K starts at 9:00 AM. The start sits about 890 feet above sea level.
Fees exclude processing fees. Comparisons use current entry fees and published results from races nearby.
Start location and course
1327 Wall Street, Oconomowoc, WI 53066
The pin marks the address the race lists, which is usually the start. The organizers have not shared a course map with us yet.
Typical race-day weather
Around November 7 the day usually runs from 37°F at dawn to 53°F in the afternoon, with measurable rain on about 20% of days. Cold snaps dip to 26°F and hot years reach 66°F.
Based on 70 days within a week of the date over the last 5 years, from historical weather for the start area. Not a forecast.
Race details
- Where
- 1327 Wall Street, Oconomowoc, WI 53066Map
- Course
- Road
- Start elevation
- About 890 feet
- Included with entry
- T-Shirt
- Donations
- Accepted when you register
- Distances
- 5K, 10K, Half Marathon
- Editions
- 2026 (Nov 7, 2026), 2025 (Nov 8, 2025), 2024 (Nov 9, 2024), 2023 (Nov 11, 2023), 2022 (Nov 12, 2022), 2021 (Nov 6, 2021)
Organize this race? Add details or a correction
Plan your race
Quick answers
- When is Chilly Willy Winter Run Series - SEVEN Events!?
- Saturday, November 7, 2026, starting at 9:00 AM.
- How much does it cost?
- Entry starts at $215 before processing fees.
- When does registration close?
- Online registration closes Dec 10, 2026, unless the race fills first.
- Is the entry fee high for Wisconsin?
- At $215, entry is about 231 percent above a typical half marathon in Wisconsin, which costs $65 right now.
- Do runners get a shirt or medal?
- Entry includes a shirt, according to the race's registration page. Check it for sizes and whether kids' races get the same.
- Can I donate to a cause when I register?
- Yes. The registration form offers an optional donation, usually for the charity or nonprofit the race supports. The race's own page names the cause.
- What distances can I run?
- 5K, 10K, Half Marathon.
- Where does it start?
- 1327 Wall Street, Oconomowoc, WI 53066.
From the organizers
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.)