Chilly Willy

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

The Wisconsin Chilly Willy Winter Run Series is comprised of seven 5K races.  At the Last Call & First Call race, there is an option to run 5K, 10K or 1/2 marathon.  When registering for the series, you will have the option of choosing to run either of the 10K's or 1/2's at no additional charge.

This year we are excited to announce that 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 November 4 Register | More Info Results
Great Gobble Wobble 5K (Milwaukee or Oconomowoc) November 23 Register | More Info Results
Last Call 5K, 10K & 1/2 Marathon December 3 Register | More Info Results
Waukesha Janboree Frosty 5K January 27  Register | More Info Results
Flannel 5K & 10K February 24 Register | More Info Results
Shake Your Shamrocks 5K, 10K & 2 mile walk March 17  Register | More Info Results
First Call 5K, 10K & 1/2 Marathon  March 31 Register | More Info Results
Series Registration   Register | More Info  

Series Registration Includes

  • Entry into all 7 races (5K, 10K or 1/2 marathon distances)
  • Custom Chilly Willy hoodie
  • Chilly Willy race bibs with your name printed on them
  • $20 off a purchase of shoes at Endurance House Delafield
  • All the SWAG from each race
  • Random gift certificates from Endurance House Delafield & Silver Circle Sports Events
  • 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

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 10/24/17 for the first race).

Kiddos Race for FREE

There will be a Kids 1K run (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.

Winter Training

This year we are excited to announce that 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.

Endurance House provides training in a team environment for runners of all abilities.  In addition to the many benefits of the Endurance House Run Team, new members who join by October 15th will receive a training plan for the entire Chilly Willy Series AND $15.00 off of your series registration!

Hot Chocolate Bar FREE

New for 2017 / 2018!  All races will have the Silver Circle hot chocolate bar.  The First Call and Last call will have our fresh fruit bar. 


Series Pricing

Through August $160
September $175
October $185
November $195
Race Day $200
Kiddos FREE

Opt out of a shirt+hoodie and save $25 on the series.

Individual Race Price

Schedule 5K / 10K Half Marathon
Now - four weeks prior to race $25 $40
Four weeks - two week prior to race $30 $45
Two weeks - race day $35 $50
Race Day $40 $55
Kiddos Race - FREE    

Runners must participate in 5 races to be eligible for 5K series awards. You are welcome to run the 10K or 1/2 marathon distances but points will not be allocated to the 5K series awards.  All age groups are based on the age of the runner at the end of the year (2018).  

Series rules

Age group medals & half marathon finisher medals.

Average Joe Award

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.


The race is chip timed by Silver Circle Sports Events, LLC.

How to wear your bib.


See individual race for instructions.


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.







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 friend 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 Flannel 5K Shake Your Shamrocks First Call Total
Endurance House 3 3 3 3 3     9
Silver Circle Sports 6 12 5 7 5     23
Hares and the Tortoises 13 12 8 16 12     33
TrailGators 6 5 4 10       15
Get er run!     4          
Falls XC     10          
Running DILFS     32          
Two Girl's & a Farm Athletic Team     66          

Overall Chilly Willy Standings

The Mother Nature Factor

Please note, that 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.