Chilly Willy Winter Run Series
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Winter Run Series 2026-2027
This is the 22nd running of the Winter Run Series, a set of six running events held across Milwaukee and its suburbs between October 25, 2026 and March 14, 2027. Each event offers short distance road race options and takes place in a different Milwaukee area community.
The six events in the series take place as follows: Pumpkin Run in Oconomowoc on October 25 2026; The Elf Run in Hales Corners on November 22 2026; Run Into The New Year in Wauwatosa on December 31 2026; The Big Chill in South Milwaukee on January 17 2027; The Cupid Shuffle in Shorewood on February 14 2027; and Luck of the Irish in West Allis on March 14 2027.
Distances offered at each event include:
- 5K
- 10K
A six event series registration bundle is available for the full sequence. The bundle is linked to a series medallion that is awarded only to participants registered for all six events. Individual event registration fees are listed as $30.00 and the six event series registration fee is listed as $0.00 in the event information. Visit the organization's website for the most recent information.
