Chilly Willy Winter Run Series - SEVEN Events!
Chilly Willy Winter Run Series - SEVEN Events! is a running and rucking race on November 7, 2026 – March 20, 2027 in Oconomowoc, WI, with an entry fee of $180.
- Date
- November 7, 2026 – March 20, 2027 (107 days to go)
- Location
- 1327 Wall Street, Oconomowoc, WI
- Price
- $180
- Sports
- RunningRucking
From the Organizer
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. 👕💰- 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!
Events
Weather
Typical Conditions
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
50°
Typical Low
32°
Chance of Rain
34%
Based on US Climate Normals data from Oconomowoc Wwtp, 2 mi from the venue.
Host City
About Oconomowoc, WI
Population
18,385
as of 2023
City Elevation
868 ft
Nearest Airport
MKE
General Mitchell International Airport · 32 mi
Time Zone
Central Time
From Endurance Grid
A mid-size host city. Enough lodging and amenities to keep race weekend easy, without big-city sprawl.
Race Location
Your Next Start Line
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at Chilly Willy Winter Run Series - SEVEN Events!, put it on the calendar, and turn “someday” into a start date.
107
Days to train
- Race
- Chilly Willy Winter Run Series - SEVEN Events!
- Date
- November 7, 2026 – March 20, 2027
- Location
- 1327 Wall Street, Oconomowoc, WI
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From Endurance Grid
About These Sports
This race spans more than one sport — here’s a guide to each, so you can understand what’s involved and decide if it’s the right fit. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.
Running
From 5K to marathon, running races are an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Rucking
Covering a distance on foot under a weighted rucksack — from timed solo challenges to longer team events.
Coming Up
More Running races near Oconomowoc, WI
Lake Country Half Marathon
8 Mile · Half Marathon · From $65 · 104 E Wisconsin Ave
1 mile away
Mama K's Cookie Run
1K · 5K · From $5 · 104 E. Wisconsin
1 mile away
DoLittle Marathon
5K · 10K · Half Marathon · Marathon · From $32.50 · Rosevelt Park
2 miles away
Zachariah's Acres Fall Run, Walk & Roll
5K · Half Marathon · From $25 · N74 W35911 Servants' Way
2 miles away
Plan your trip
Make it a Racecation
Coming from out of town? There's more to Oconomowoc than race day. We'll help you line up nearby lodging, flights, a rental car, and things to do so you can make the most of your racecation.
Plan your trip to OconomowocFrequently Asked Questions (FAQs)
What is the Chilly Willy Winter Run Series - SEVEN Events!?+
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Chilly Willy Winter Run Series - SEVEN Events!
Nov 7, 2026