Winter Run Series™ 2026 — Oconomowoc, WI

Date
October 25, 2026
Location
Oconomowoc, WI
Venue
Milwaukee Area
Start Time
9:00 AM
Entry Fee
$0.00 – $50.00
Events
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
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The Winter Run Series kicks off at 9:00 AM in Oconomowoc, Wisconsin, giving traveling runners time to arrive the morning of the race. Held in the Milwaukee area on October 25, 2026, this running event offers accessible entry fees ranging from free to $50. The series is designed for runners looking to compete during the fall-to-winter transition period. Registration and logistics are straightforward, making it an option worth considering if you're scheduling a race weekend in Wisconsin. Check the race's official details for specific distances and course information before booking your travel.

From the Race Organizer
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

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Winter Run Series™ 2026 — Oconomowoc, WI

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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
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support
Get a Quote — Faye Travel Insurance

Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.

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Frequently Asked Questions

When is Winter Run Series™ 2026 — Oconomowoc, WI?

Winter Run Series™ 2026 — Oconomowoc, WI takes place on October 25, 2026. The race is held in Oconomowoc, Wisconsin.

Where is Winter Run Series™ 2026 — Oconomowoc, WI held?

Winter Run Series™ 2026 — Oconomowoc, WI is held at Milwaukee Area in Oconomowoc, Wisconsin.

Where can I find hotels near Winter Run Series™ 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.