Chilly Willy Winter Run Series - SEVEN Events!
- Date Sat 8th November 2025 - Sun 22nd March 2026
- Time 9:00AM CST
- Location Oconomowoc, Wisconsin
- Price $238.10
- Races 5 races
- Distances 10km, Half Marathon
Event summary
Get ready to embrace the chill and join the excitement at the Chilly Willy Winter Run Series, taking place from November 8, 2025, to March 22, 2026, in the scenic city of Oconomowoc, Waukesha. This thrilling winter series features seven electrifying events, including 5K and 10K races at most venues, as well as two half marathons that will keep you motivated through the colder months.
New for this year, participants can also try their hand at rucking, a fantastic fitness activity that combines walking or hiking with a weighted backpack. Whether you're racing solo or forming a team, there's something for everyone in this community-focused series. With awards for overall winners, age group champions, and team series champions, you won’t want to miss out on the fun. Bundle up, lace up, and get ready for the ultimate winter running adventure in Wisconsin!
New for this year, participants can also try their hand at rucking, a fantastic fitness activity that combines walking or hiking with a weighted backpack. Whether you're racing solo or forming a team, there's something for everyone in this community-focused series. With awards for overall winners, age group champions, and team series champions, you won’t want to miss out on the fun. Bundle up, lace up, and get ready for the ultimate winter running adventure in Wisconsin!
Organiser's Description
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 youd still like to register for the All Access Pass, select Registered After T-Shirt Deadline during signup, then email us to let us know youd like to upgrade. Well 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
-------------------------
202526 WISCONSIN CHILLY WILLY WINTER RUN SERIESSNOWFLAKEMALE SIGNFEMALE SIGN
PRESENTED BY SILVER CIRCLE SPORTS EVENTS, LLC
Bundle up and lace upOLD MAN WINTER IS READY TO RACE! snowflake Join us for the 202526 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 backpackalso 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.
Dont miss your chance to experience WISCONSIN WINTER RUNNING AT ITS BEST. Run one raceor run them all. Either way, well see you at the start line!
Ready to run? Register now! [https://runsignup.com/Race/Register/?raceId=48935]
-------------------------
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 youd still like to register for the All Access Pass, select Registered After T-Shirt Deadline during signup, then email us to let us know youd like to upgrade. Well 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
-------------------------
202526 WISCONSIN CHILLY WILLY WINTER RUN SERIESSNOWFLAKEMALE SIGNFEMALE SIGN
PRESENTED BY SILVER CIRCLE SPORTS EVENTS, LLC
Bundle up and lace upOLD MAN WINTER IS READY TO RACE! snowflake Join us for the 202526 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 backpackalso 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.
Dont miss your chance to experience WISCONSIN WINTER RUNNING AT ITS BEST. Run one raceor run them all. Either way, well see you at the start line!
Ready to run? Register now! [https://runsignup.com/Race/Register/?raceId=48935]
-------------------------
Races
-
Chilly Willy Winter Run Series 5K
Incl. $18.10 Fee & T-Shirt
Sat 8th November 2025 (9:00AM CST)
$238.10
CLOSED -
Chilly Willy Winter Run Series 10K
Incl. $18.10 Fee & T-Shirt
Sat 8th November 2025 (9:00AM CST)
$238.10
CLOSED -
Chilly Willy Winter Run Series Half
Incl. $18.10 Fee & T-Shirt
Sat 8th November 2025 (9:00AM CST)
$238.10
CLOSEDSeries runners who select the half marathon option will be automatically dropped to the 10K distance for races that do not have a half marathon distance. -
Chilly Willy Winter Walk Series
Incl. $18.10 Fee & T-Shirt
Sat 8th November 2025 (9:00AM CST)
$238.10
CLOSED -
Chilly Willy Winter Ruck Series 5K
Incl. $18.10 Fee & T-Shirt
Sat 8th November 2025 (9:00AM CST)
$238.10
CLOSED
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1327 Wall Street, The Greatest Place on Earth - WISCONSIN!, Oconomowoc, 53066, WI, United States
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Chilly Willy Winter Run Series - SEVEN Events!
