Chilly Willy Winter Run Series - SEVEN Events!

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 popular, low-impact workout for people of all fitness levels.
  
  Ready to give it a try? Load up your pack and take on a 5K ruck at any of our events.
  
  Please note: Rucking events are timed, but there are no age group awards.

  🏅 Awards will be presented to overall, age group, and team series champions.

Don’t miss your chance to experience Wisconsin winter running at its best. Run one race—or run them all. Either way, we’ll see you at the start line!

Ready to run? Register now!

Join fellow runners on November 7, 2026 for the Chilly Willy Winter Run Series - SEVEN Events!. It's a fantastic 5K, 10K, Half-Marathon featuring a flat and fast course in Oconomowoc.