Chilly Willy Winter Run Series - SEVEN Events!

11/9/20025 - Registration Update Registration has closed for the series. If you would like to attend the series, please contact us and we will open it for you. ️ 10/29/2025 – T-Shirt Deadline Update The t-shirt deadline has now passed. Series runners will be contacted after Veterans Day to confirm their shirt size. Shirts will be handed out at future events in the series. If you’d still like to register for the All Access Pass, select “Registered After T-Shirt Deadline” during signup, then email us to let us know you’d like to upgrade. We’ll take care of the rest and move you into the pass. Thanks for keeping those miles (and emails) coming! — Sean K. Osborne Chief T-Shirt Sorter  2025–26 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 2025–26 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, a