Wisconsin Chilly Willy Series
2025–26 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 2025–26 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 every event
- 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!
🏅 Awards will be presented to overall, age group, and team series champions.
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 backpack—also 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 or 10K ruck at any of our events.
Please note: Rucking events are timed, but there are no age group awards.
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!
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
Chilly Willy Winter Ruck Series 10K
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.
New for 2025/2026 - Wisconsin Chilly Willy Series All Access Pass
🚀 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. 🌲
Finisher Woodles & Awards
Your 2025-2026 Finisher Woodles!
A medal... made of wood... also known as a Woodle! Every finisher, no matter the distance, will receive one!
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!
*2025 - 2026 Woodles will be displayed soon! Below are the 2024 - 2025 Finisher Woodles.
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 8, 2025
📍 Milwaukee War Memorial
Great Gobble Wobble 5K (Milwaukee)
📅 Thursday, November 27, 2025
📍 Boerner Botanical Gardens
Great Gobble Wobble 5K & 10K (Oconomowoc)
📅 Thursday, November 27, 2025
📍 Fowler Park
Last Call 5K, 10K & Half Marathon
📅 Sunday, December 7, 2025
📍 Glacial Drumlin Trail, Waukesha
Frosty 5K
📅 Saturday, January 24, 2026
📍 Frame Park, Waukesha
Flannel 5K & 10K
📅 Saturday, February 7, 2026
📍 Menomonee Park
Shake Your Shamrocks 5K, 10K & 2-Mile Walk
📅 Saturday, March 7, 2026
📍 Lucky Chucky’s Beach Bar, Oconomowoc
First Call 5K, 10K & Half Marathon
📅 Sunday, March 22, 2026
📍 Glacial Drumlin Trail, Waukesha
T-Shirts
All New Race Shirts for the 2025-26 Season!
Images Coming Soon!
Series Awards
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 3/24/2025.
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 2025–26 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 a Silver Circle Sports Events, LLC owned, produced, timed & managed event. 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
