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Chilly Willy Winter Run Series - SEVEN Events!

Sat November 9 - Sun March 23, 2025 Oconomowoc, WI 53066 US


Chilly Willy Winter Run Series 5K

$180 9:00AM CST - 12:00PM CDT Price increases after June 28, 2024 at 11:59pm CDT
Walker Friendly!

Chilly Willy Winter Walk Series

$180 9:00AM CST - 12:00PM CDT Price increases after June 28, 2024 at 11:59pm CDT

Chilly Willy Winter Run Series 10K

$180 9:00AM CST - 12:00PM CDT Price increases after June 28, 2024 at 11:59pm CDT

Chilly Willy Winter Run Series Half

$180 9:00AM CST - 12:00PM CDT Price increases after June 28, 2024 at 11:59pm CDT


Lace up your shoes and grab your cold weather gear because Old Man Winter is knocking at your door looking for a running partner. Join Silver Circle for the 2024-25 Wisconsin's Chilly Willy Winter Run Series. All SEVEN races are back this year and you'll have plenty of opportunity to race in everyone's favorite time of the year - winter! Race the series as an individual or grab some friends and race as a team. All races have a 5K and 10K option, and two races have the option for a half marathon distance (series runners who select the half marathon distance will automatically be dropped to the 10K distance for races without a half marathon distance). Awards will be given to the overall age group and team series winners.

Seven Awesome Races!

How To Register

Registering for the series
Select the distance you want to run. If you select half marathon, we will automatically put you in the 10K distance at races where there isn't a half. The same is true for the 10K. This will register you for the entire 2024-25 winter run series. Please make sure you only select one Gobble Wobble race unless you have mastered how to be in two places at once.

Register for Single Races
Individual Race Registration will open later in the year - check back soon form more information.

Kiddo's 1K Registration
As always, our kiddos races are free at all of the Chilly Willy Races.

Series Schedule

Individual race registration will open later in 2024. You can take a look at the race websites to find more information about individual races, but please note that some details may change. 

2024-2025 schedule:


All New Race Shirts for the 2024-25 Season!

Available soon!

Series Awards

2023-2024 | 2022-2023 | 2021-2022 | 2020-2021

Runners must participate in 4 of the races to be eligible for 5K OR 10K series awards. If you run the half marathon, you will be awarded 5 points regardless of placement in the half. You can switch between distances (at no cost) but you must run in at least 4 races of the same distance.  

The overall male and female winner for the 5K and 10K series will receive a free entry into the 2024-25 series and series trophy.

Overall age group medals and awards will be distributed at a wrap up event that will be scheduled and announced after the last race in the series.

Series Rules

  • To be eligible for the final championship awards, runners must have participated in four of the seven races.
  • Awards will be based on a point system (1st place: 10 points, 2nd place: 9 points, 3rd place: 8 points, through 10th place).  
  • All runners receive one point for finishing regardless of ranking.  
  • Division winners (5K & 10K) will be allocated 11 points and those points will be added to their age group ranking.
  • In the event of a tie, age will be the tie breaker with the oldest individual winning.  
  • Series points will be calculated on the total points an athlete accumulates in that division.  
  • In the event no one wins 4 events to be eligible for the overall winner, the individual with the most cumulative points will be the winner.  If there is a tie, the oldest runner will be crowned the champion.  
  • All age groups are based on the age of the runner on 3/24/2024.


As part of our effort to increase awareness of run local/buy local, we have created the Chilly Willy Running Team Challenge. The goal is to increase awareness of local running managers (hey, that’s us), local running stores (hey, that’s where you shop) and local running teams (hey, that’s all of us) in a fun and competitive format. 

Grab three of your friends and create a team. Hey, it's free and you can create the team during registration.

How it works.

Hot Chocolate Bar!

It's back for the 2024-25 Chilly Willy Series Races -- Our famous hot chocolate bar!!!

Meet your friends after the race for a quick warm up at our hot chocolate bar. Complete with a huge selection of the tastiest treats, you'll find all you need to make a great cup of hot Chocolate after a cold run. You'll find our hot chocolate bar at all of our 2024-25 Chilly Willy Series runs, except for the Shake Your Shamrocks race (possibly the First Call as well depending on the weather). We'll also typically announce awards after the race over a nice cup of hot chocolate, so its definitely the place to be after the race!

Average Joe & Jane Awards

The Average Joe & Jane Awards are back for the Chilly Willy Series 5K Runs are are presented to the male and female runner who finished in the exact middle of all runners. Winners will receive a t-shirt and custom medal! 

The Mother Nature Factor

Occasionally the event distance will not be exact because roads end, highways get in the way, cattle stampede, and it snows in Wisconsin. We do our best to ensure all event distances are exact, but occasionally mother nature happens.

Packet Pickup

Please see the individual race website for packet pickup instructions.

Silver Circle Sports Events

This series is a Silver Circle Sports Events, LLC owned, produced, timed & managed event. Need help with an event? Contact us HERE.

Race Contact Info

If you have any questions about this race, click the button below.


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