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
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.) New This Year: Rucking! We're excited to introduce Rucking to all Chilly Willy Winter Series events! Rucking is a fitness activity that combines walking or hiking with a weighted backpack—also known as a rucksack. Originating from military training, rucking has become a popula
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
