Chilly Willy

All races now have buildings at the start / finish line!

Are you ready to beat old man winter?  Join Silver Circle Sports Events for Wisconsin's Chilly Willy Winter Run Series.  Eight races during everyone's favorite time of the year - winter!  Choose from a winter 5K distance, 10K or 1/2 marathon.

For the second year,  the Chilly Willy Run Series is presented by Endurance House Delafield.  Endurance House is not only Lake Country’s top provider of running shoes, clothing, and equipment, they can also satisfy your biking and swimming needs.

Charity Partner

MS Run the US, Inc. is dedicated to raising awareness and funds to support multiple sclerosis (MS) research, while also supporting those living with disability due to MS. Our running events focus on promoting a healthy lifestyle while inspiring individuals to maximize their capabilities and become more active to help those in need.

Race Schedule 

Race Schedule Date    
Vets Day 5K & 10K Saturday November 10 Register | More Info Results
Great Gobble Wobble 5K (Milwaukee) Thursday November 22 Register | More Info Results
Great Gobble Wobble 5K & 10K (Oconomowoc) Thursday November 22 Register | More Info Results
Last Call 5K, 10K & 1/2 Marathon Sunday December 2 Register | More Info Results
Waukesha Janboree Frosty 5K & 1K Pancake Run Saturday January 26 Register | More Info Results
Frostbite 5K Saturday February 16 Register | More Info Results
Flannel 5K & 10K Saturday February 23 Register | More Info Results
Shake Your Shamrocks 5K, 10K & 2 mile walk Saturday March 16 Register | More Info Results
First Call 5K, 10K & 1/2 Marathon  Sunday March 31 (TBD) Register | More Info Results
Series Registration      

Series Registration Includes

  • Entry into all 8 races (5K, 10K or 1/2 marathon distances)
  • Chilly Willy race bibs with your name printed on them
  • FREE photos from Focal Flame Photography
  • FREE entry into the Pancake 1K
  • Random gift certificates from Silver Circle Sports Events & Endurance House Delafield
  • A professionally run event by one of Wisconsin's largest race companies
  • Chip timed by Silver Circle Sports Events
  • Kids can race the kiddos race for free
  • Finishers medal for everyone registered for the series.
  • FREE hot chocolate bar & fresh fruit bar at First Call and Last Call
  • Discounted Chilly Willy Merchandise

Free Race Photos

Silver Circle Sports Events is excited to bring Focal Flame Photography’s professional FocalShare race photo service to the Chilly Willy race series.

Participants: you will get FREE downloads of high-resolution digital race photos, searchable by your bib number, within a few hours of crossing the finish line. As soon as photos are ready, you'll receive an email with links to your FocalShare photos online. You an also share them easily using the Silver Circle Facebook app, and a free iOS app for the iPhone and iPad.

Custom Race Bibs

All runners will receive a custom Chilly Willy bib.  Series runners will have their name printed on them (must be registered by 10/24/18 for the first race).  If you register after 10/24/2018, we will have your bibs ready for you at the other races.

Kiddos Race for FREE

There will be a Kiddo's 1K run at all runs for kiddos under 10.  All kids will get a race bib and finisher medal.  The race is FREE for the kiddos if mom or dad is registered and you can register on line at no charge.  Sorry no shirts for the kiddos.

Hot Chocolate Bar FREE


All races will have the FREE Silver Circle Sports hot chocolate bar.  The First Call and Last call will have our fresh fruit bar. 

Series Pricing

August 14 at Endurance House $160
August - September $175
October $185
November - until the Vets Day 5K / 10K $195
November 11 - 22nd $165
Kiddos FREE

If you run the Vets Day 5K / 10K and decide you want to run the series, we will credit your entry fee towards the series.

Individual Race Price

Schedule 5K / 10K Half Marathon
Now - four weeks prior to race $27.50 $40.00
Four - Three Weeks $30.00 $42.50
Three - Two Weeks $32.50 $45.00
Two - One Week $35.00 $50.00
One Week - Race Day  $37.50 $52.50
Race Day $40.00 $55.00
Kiddos FREE    


Official Running Store Partner

Run the Chilly Willy Winter Run Series with the best local running and training community in the area - Endurance House in Delafield.


Individual race Awards

Overall Male & Female in each division will receive plaques & flowers.  Top 3 male & female finishers in 5 year age groups will receive a custom medal. Half marathon finishers receive a custom finisher medal.

Average Joe & Jane Awards 

At all Silver Circle Sports Events 5K, we will award the Average Joe & Jane award.  The award goes to the male and female that finish exactly in the middle of their division will received receive a super sexy Average Joe / Average Jane shirt, flowers and an free entry into the Average Joe 5K.

Series Awards

Runners must participate in 5 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.

If there is not a runner who has won 5 races in the series, the individual with the most points (male & female) will be crowned the overall winner.  In the event of a tie, the older runner will be winner.

Overall age group medals and awards will be distributed at the wrap up event.

All age groups are based on the age of the runner on 3/31/2019.

Series rules 







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

Team Standings

Team Vets Day Gobble Wobble Last Call Frosty 5K Frostbite 5K Flannel 5K Shake Your Shamrocks First Call Total
MS Run The US 5 9 7 6       7 34
Endurance House 14 10 4 16 11   11 10 76
Trailgators     17            
Coming For You                  
Glacial Trail Winners                  
Lunatic Limbs 10 12   10   6   5 43
#TeamSCSE 4 5 4 4 4 4 4 4 NA
Where is your team?                  
Running Runkes     30            
Crazy Cousins     59            
Dunder Mifflin     17            
TGIT     31            
Team Bean       9          
Team Phoenix       12          
Nature Hill         19   11    
Flannel Planners           17      
RunningSharksDooDoo           22      
SmILE Like Amanda           15   16 31
Wild           11      
Cambridge             34    
Fit, Fierce, & Fabulous               22  

Points document

2017 - 2018 Team Challenge Winners

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 events are exact distances exact but occasionally mother nature happens.


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


Shirts will be gender specific at the First Call and Last call. All other races will have unisex cotton shirts.


We need volunteers for everything from goody bag stuffing to course marshals. If you or your group have an interest in volunteering, we would greatly appreciate the assistance.  All volunteers can run a future race at no charge.  Contact us for more info.

Weather / Refund Policy: 

Refunds are not permitted for any reason.

The event will be held unless severe weather occurs. In the event of severe weather, the race director may delay or cancel the event.  If the event is canceled, there will be no refunds. Silver Circle Sports Events has a NO REFUND policy.