Winter Run Series™

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!