Events
Chilly Willy Winter Run Series 5K
Chilly Willy Winter Run Series 10K
Chilly Willy Winter Run Series Half
Chilly Willy Winter Walk Series
Chilly Willy Winter Ruck Series 5K
Wisconsin Chilly Willy Series
2026–27 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 2026–27 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.) -
🚀 Skip the Lines With The CW All Access Pass! 🏃♂️
CW All Access Pass?
Your ticket to skipping the packet pickup line and heading straight to the start line!How It Works:
✔ Register for the series in any distance 🏅
✔ Opt out of a shirt and save $10 👕💰- this automatically gets you the pass
✔ Receive a reusable ankle strap for timing ⏱️
✔ No check-in required – just show up and run! 🏃♂️🚀More running, less waiting—because race day should be running, not the lines. 🌲
🏅 Awards will be presented to overall, age group, and team series champions.
Don’t miss your chance to experience Wisconsin winter running at its best. Run one race—or run them all. Either way, we’ll see you at the start line!
Ready to run? Register now!
How to Register
Registering for the Series
Select the distance you would like to run for the series. If you register for the half marathon, you will automatically be placed in the 10K at races that do not offer a half marathon.
The same applies to 10K runners at the Frosty 5K. Since there is no 10K distance at that event, all 10K series participants will automatically be placed in the 5K.
Registering for the series will sign you up for the entire 2026–27 Chilly Willy Winter Run Series.
Registering for Single Races
Individual race registration will open later in the year. Please check back soon for more information.
Kiddos 1K Registration
As always, kiddos races are free at all Chilly Willy Winter Run Series events. Registration is required, but there is no charge.
Finisher Woodles & Awards
Your 2026-2027 Finisher Woodles!
A medal... made of wood... also known as a Woodle! Every finisher, no matter the distance, will receive one! Each Woodle has a magnet on the back so you can show off your achievements on your fridge.
Crafted by Ridgeway Woodworks, these unique awards are made from reclaimed wood—so they’re not just stylish, they’re also eco-friendly, helping to reduce waste!
Series Schedule
You can visit the individual race websites for additional event details. Please note that all information is subject to change as race day approaches. We recommend checking back regularly for the most up-to-date updates.
2025–2026 Race Schedule
Veterans Day 5K & 10K
📅 Saturday, November 7, 2026
📍 Milwaukee War Memorial
Great Gobble Wobble 5K & 10K (Oconomowoc)
📅 Thursday, November 26, 2026
📍 Oconomowoc High School
Last Call 5K, 10K & Half Marathon
📅 Sunday, December 6, 2026
📍 Glacial Drumlin Trail, Waukesha
Frosty 5K
📅 Saturday, January 23, 2027
📍 Frame Park, Waukesha
Flannel 5K & 10K
📅 Saturay, February 13, 2027
📍 Menomonee Park
Shake Your Shamrocks 5K, 10K & 2-Mile Walk
📅 Saturday, March 13, 2027
📍 Lucky Chucky’s Beach Bar, Oconomowoc
First Call 5K, 10K & Half Marathon
📅 Sunday, March 21, 2027
📍 Glacial Drumlin Trail, Waukesha
T-Shirts
All-new race shirts for the 2026–27 season!
Each Chilly Willy Winter Run Series event will feature its own race shirt:
Vets Day 5K — Cotton unisex
Gobble Wobble 5K — Cotton unisex
Last Call 5K — Gender-specific dry wick
Frosty 5K — Cotton unisex
Flannel 5K — Cotton unisex
Shake Your Shamrock 5K — Cotton unisex
First Call 5K — Gender-specific dry wick
Long sleeve shirts are available at all events for a small upgrade fee.
Series Awards
2025-2026 | 2024-2025 | 2023-2024 | 2022-2023
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 3/21/2027.
Walkers Welcome!
We’re thrilled to offer a walker division as part of the Wisconsin Chilly Willy Series! Whether you're walking for fun, fitness, or competition, we encourage you to join us and enjoy the race at your own pace. To ensure a smooth and enjoyable experience for all participants, we kindly ask that walkers stay to the right side of the road. This allows runners to pass safely on the left and helps maintain a steady flow throughout the course.
Thank you for being part of the Chilly Willy community—we can’t wait to see you at the starting line!
🏃♂️ Team Challenge: Run Local, Win Local 🏆
Introducing the Chilly Willy Running Team Challenge — part of our commitment to supporting the Run Local / Buy Local movement!
Our goal? To shine a spotlight on:
👟 Local race organizers (that’s us!)
🛍️ Local running stores (that’s where you shop!)
💪 Local running teams (that’s YOU!)
It’s a fun and competitive way to build team spirit, support the local running community, and make winter racing even more awesome. Rally your squad and get ready to run together, cheer each other on, and maybe even take home some team bragging rights!
Grab three of your friends and create a team. Hey, it's free and you can create the team during registration.
How it works.
☕️ The Famous Hot Chocolate Bar is Back! ❄️🍫
Returning for the 2026–27 Chilly Willy Winter Run Series—it's everyone's favorite post-race tradition: the Hot Chocolate Bar!
After you cross the finish line, warm up with friends at our delicious hot chocolate station, loaded with a huge selection of sweet toppings and mix-ins to create your perfect cup. It’s the ultimate reward after a frosty run! You'll find our Hot Chocolate Bar at every Chilly Willy Series race.
🏅 We’ll also be announcing awards post-race—and there's no better way to celebrate than with a cup of cocoa in hand! The hot chocolate bar is definitely the place to be after the race.
Come for the run, stay for the chocolate! 🍫☕️
The Mother Nature Factor
Sometimes, Mother Nature has her own race plan. While we strive to ensure every course is measured accurately, real-world factors can occasionally impact the exact distance.
From dead-end roads to unexpected highway crossings, wandering cows, or good ol’ Wisconsin snowstorms, things happen. We promise to do our best to keep the course as accurate as possible—but if it’s a little off, now you know why.
Thanks for rolling with it—just part of the adventure! 🏃♀️❄️
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!
Packet Pickup
Please see the individual race website for packet pickup instructions.
Silver Circle Sports Events
This series is owned, produced, timed, and managed by Silver Circle Sports Events, LLC, a veteran-owned event management company based in Oconomowoc, Wisconsin.
Silver Circle Sports Events provides professional race management, chip timing, registration support, course logistics, equipment, marketing support, and race-day operations for running, walking, rucking, and multisport events throughout Wisconsin.
Planning an event of your own? Whether you are organizing a 5K, walk, fundraiser, corporate wellness event, or full race production, we can help bring it to life.
Need help with an event? Contact us HERE.
Refund Policy
Refunds are not permitted for any reason including but not limited to blizzard, tsunami, hurricane, typhoon, earthquake, tornado, derecho storm, hail, lightening, thunder, zombie apocalypse, locust attack, oversleeping, birth, death, taxes, IRS audit, engagements, marriage, divorce, jail, Elvis sighting, Beatles reunion, stampede, war, peace, nuclear explosion, Packers Super Bowl win, Blob attacks, not training enough, training too much, poor prior planning or our favorite, "I forgot".
While there are no refunds, you can get referrals, transfer your bib, change your shirt size, defer your registration until next year or change your distance.
More info at https://silvercirclesportsevents.com/refund-referrals-exchanges-transfers
Sponsors
