the Winter Run Series™ - 6 Event Series Registration, The Pumpkin Run - 5K/10K, The Elf Run 5K/10K, Run Into the New Year 5K/10K, The BIG Chill 5K/10K, The Cupid Shuffle 5K/10K
The 22nd running of Wisconsin’s largest running series is set to explore the inner workings of Milwaukee and its beautiful suburbs. This series plays host to six events throughout the winter season, surrounding your favorite holidays. Bring the family to participate in the 5K or 10K. Let's Conquer the Cold! The Pumpkin Run | Sunday, October 25 | Oconomowoc, WI The Elf Run | Sunday, November 22| Hales Corners, WI Run Into The New Year | Wednesday, December 31 | Wauwatosa, WI The Big Chill | Sunday, January 17 | South Milwaukee, WI Cupid Shuffle | Sunday, February 14 | Shorewood, WI Luck of the Irish | Sunday, March 14 | West Allis, WI 6 EVENT SERIES REGISTRATION BUNDLE Join us for the 2026-2027 Winter Run Series! Start the series off with the Pumpkin Run and finish with the Luck of the Irish while completing The Elf Run, Run Into The New Year, The Big Chill, and The Cupid Shuffle in between! **Must sign up for the 6 Event Series to earn the series medallion!
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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Race Travel Insurance
Don't forget travel insurance for October 25.
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
