Chilly Willy Winter Run Series - SEVEN Events!
- Date
- November 7, 2026 – March 20, 2027
- Location
- 1327 Wall Street, Oconomowoc, WI
- Distance
- Chilly Willy Winter Run Series 5K · Chilly Willy Winter Run Series 10K · Chilly Willy Winter Run Series Half & more
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 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!
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, 1 mi from the venue.
Host City
About Oconomowoc, WI
Population
18,385
as of 2023
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.
152
Days to train
- Race
- Chilly Willy Winter Run Series - SEVEN Events!
- Date
- November 7, 2026 – March 20, 2027
- Location
- 1327 Wall Street, Oconomowoc, WI
Coming Up
More Running races near Oconomowoc, WI
Silver Circle Trivia - Ocon
Less than a mile away
Lake Country Freedom 5K, 10K & 25K
25K · 10K · 5K
Less than a mile away
Silver Circle Sunday Funday
Less than a mile away
Lake Country Half Marathon
Half Marathon
Less than a mile away
From Endurance Grid
About This Sport
Endurance Grid is here to help you understand the sport, decide if it's the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer's event page.
With running, there's a distance for every fitness level, a community at every start line, and nothing beats the feeling of crossing a finish line you trained for.
Running is an endurance sport that rewards consistency, and showing up every week compounds in ways that will surprise you.
Running
From 5K to marathon, running races are the most accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Frequently Asked Questions (FAQs)
- What is the Chilly Willy Winter Run Series - SEVEN Events!?
- Chilly Willy Winter Run Series - SEVEN Events! is a running race held in Oconomowoc, Wisconsin on November 7, 2026. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more running races near you or explore our sports guides to learn what race day actually feels like.
- When and where is the Chilly Willy Winter Run Series - SEVEN Events!?
- Saturday, November 7, 2026 in Oconomowoc, Wisconsin at 1327 Wall Street, Oconomowoc, WI. Check the event page for exact start times and wave schedules.
- How do I register for the Chilly Willy Winter Run Series - SEVEN Events!?
- Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.
Chilly Willy Winter Run Series - SEVEN Events!
Nov 7, 2026