Chilly Willy Winter Run Series – SEVEN Events! 2026 — Oconomowoc, WI

Date
November 7, 2026
Location
Oconomowoc, WI
Venue
1327 Wall Street
Start Time
9:00 AM
Entry Fee
$120.00 – $235.00
Events
Chilly Willy Winter Run Series 5K, Chilly Willy Winter Run Series 10K, Chilly Willy Winter Run Series Half, Chilly Willy Winter Walk Series, Chilly Willy Winter Ruck Series 5K
Includes
T-Shirt
Register NowRegistration Open

The Chilly Willy Winter Run Series in Oconomowoc, Wisconsin offers rucking, running, and walking events across three distances: 3.12 miles, 6.2 miles, and half marathon. Part of a seven-event series, individual races take place at 1327 Wall Street with a typical 9:00 AM start time. Entry fees range from $120 to $235 depending on the event and distance selected. This series is designed for endurance athletes and recreational participants willing to train and compete through winter conditions. The variety of distances and sport types allows runners, walkers, and ruckers to choose their challenge level while being part of the same community event throughout the season.

From the Race 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!

Hotels Near This Race

Find accommodation close to the start line in Oconomowoc, WI. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.

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Chilly Willy Winter Run Series – SEVEN Events! 2026 — Oconomowoc, WI

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Race Travel Insurance

Don't forget travel insurance for November 7.

You've trained for months and booked a trip to Oconomowoc, WI. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.

  • Trip cancellation up to 100% of prepaid costs
  • Running events covered under standard plans — no add-ons needed
  • Trip interruption up to 150% of non-refundable costs
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support
Get a Quote — Faye Travel Insurance

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Frequently Asked Questions

When is Chilly Willy Winter Run Series – SEVEN Events! 2026 — Oconomowoc, WI?

Chilly Willy Winter Run Series – SEVEN Events! 2026 — Oconomowoc, WI takes place on November 7, 2026. The race is held in Oconomowoc, Wisconsin.

Where is Chilly Willy Winter Run Series – SEVEN Events! 2026 — Oconomowoc, WI held?

Chilly Willy Winter Run Series – SEVEN Events! 2026 — Oconomowoc, WI is held at 1327 Wall Street in Oconomowoc, Wisconsin.

Where can I find hotels near Chilly Willy Winter Run Series – SEVEN Events! 2026 — Oconomowoc, WI?

RaceHotelFinder shows hotels sorted by distance from the race venue in Oconomowoc. Use the map or list view on this page to compare options and book race weekend accommodation.