Skip to main content
triboutique.ca - Triathlon gear with free shipping over $125 triboutique.ca - Free shipping over $125 with coupon code CANADA: Triathlon Equipment, wetsuits, Swimskins and gifts.

Chilly Willy Winter Run Series - SEVEN Events!

Date:
Sat, Nov 08, 2025 at 9:00 AM – 12:00 PM
Location:
1327 Wall Street
Oconomowoc, Wisconsin
53066
United States
OpenStreetMap Google Maps
Links:
runsignup.com
Tags:
13.1 Miles 3.12 Miles 6.2 Miles Run Walk

11/9/20025 - Registration Update

Registration has closed for the series. If you would like to attend the series, please contact us and we will open it for you.

🗓️ 10/29/2025 – T-Shirt Deadline Update

The t-shirt deadline has now passed.

Series runners will be contacted after Veterans Day to confirm their shirt size. Shirts will be handed out at future events in the series.

If you’d still like to register for the All Access Pass, select “Registered After T-Shirt Deadline” during signup, then email us to let us know you’d like to upgrade. We’ll take care of the rest and move you into the pass.

Thanks for keeping those miles (and emails) coming!

— Sean K. Osborne

Chief T-Shirt Sorter 👕

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 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.)

  • New This Year: Rucking!

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 ruck at any of our events.

Please note: Rucking events are timed, but there are no age group awards.

🏅 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!

More races nearby

  • Yellow Brick Road 5K [runsignup.com]

    Sat, Jun 06, 2026 at 7:45 AM

    Description

    This year, we’re making things easier by preassembling team packets. If your team has 4 or more members by 9:00am Wednesday, June 3rd, you’ll be able to pick up the entire team’s bibs and shirts at...

    This year, we’re making things easier by preassembling team packets. If your team has 4 or more members by 9:00am Wednesday, June 3rd, you’ll be able to pick up the entire team’s bibs and shirts at packet pickup in one convenient bundle. The Team Captain may pick them up or designate someone else on the team to do so. Please only send one team member to pick up for the entire team.

    If your team does not meet the 5-member threshold, each team member can pick up their packet individually.

    📣 Important: If your team qualifies for group pickup (4+ team members), individual team members will not be able to pick up their individual packets.

    The packets will include:

    Race shirts

    Race bibs with labels (name, shirt size, bib number, gender, age and event).

    Please let your team members know if you used your email to register them, they will not receive these race day instructions or other important information, so please forward this email to them.

    The start and finish lines are downtown in front of Oz Plaza!

    Join Us for the Yellow Brick Road 5K Run/Walk!

    The Oconomowoc Area Chamber of Commerce, together with our Finish Line Sponsor, Silver Circle Sports Events, LLC, invites you to participate in this exciting summer event.

    Inspired by the historic premiere of the Yellow Brick Road in 1939, this scenic run will start and finish at City Hall, overlooking the brand-new Oz Plaza.

    Join us as we celebrate the 86th Anniversary of The Wizard of Oz! With exciting events planned throughout Oconomowoc, this is your chance to be part of the magic.

    Register Today and Receive:

    • Custom Yellow Brick Road 5K T-shirt

    • Commemorative Finisher Medal featuring the 87th-anniversary logo (while supplies last)

    • Professional Chip Timing by Silver Circle Sports Events, LLC

    • RaceJoy athlete tracking

    • Trophies for the top male and female overall winners

    • Team Challenge Trophy for group participants

    • Age Group Awards

    • Don’t miss this memorable community celebration—sign up now for the 5K run or 2-mile walk!

    Course map
    2.2 km from Oconomowoc
    174 E., Oconomowoc, Wisconsin, 53066, United States
    OpenStreetMap Google Maps

    2 Miles 3.1 Miles 5k Run Walk

  • Silver Circle Trivia - Ocon [runsignup.com]

    Thu, Jun 18, 2026 at 6:30 PM

    Description

    Looking for a fun way to spend a winter afternoon? Join Silver Circle Trivia and the Oconomowoc Beer Garden for FREE trivia! Warm up your brain and enjoy great company in a cozy atmosphere.

    Why Join...

    Looking for a fun way to spend a winter afternoon? Join Silver Circle Trivia and the Oconomowoc Beer Garden for FREE trivia! Warm up your brain and enjoy great company in a cozy atmosphere.

    Why Join Us?

    • It’s Free: No entry fee—just bring your knowledge and enthusiasm!

    • Food & Drink Specials: Oconomowoc Beer Garde will be serving delicious bites and refreshing beverages. 🍔🍹

    • Perfect Summer Fun: A great way to kick back, play some trivia and enjoy the Oconomowoc Summer!

    Important:

    Preregistration is required for the entire team so Oconomowoc Beer Garde can ensure appropriate staffing levels, assign tables and create a smooth, enjoyable experience for everyone. Don’t miss out—secure your spot today!

    Grab your friends and make it an afternoon to remember. See you there!

    Upcoming Trivia Events!

    Registration for future events will open after the most recent event happens.
    2.9 km from Oconomowoc
    104 E Wisconsin Ave, Oconomowoc, Wisconsin, 53066, United States
    OpenStreetMap Google Maps

    Run

  • Lake Country Freedom 5K & 10K [runsignup.com]

    Sat, Jul 04, 2026 at 8:45 AM

    Description

    Celebrate summer, community, and freedom at the Lake Country Freedom 5K/10K Run, Walk & Ruck in beautiful Oconomowoc, Wisconsin! Held during the city's 151st Hometown Celebration, this...

    Celebrate summer, community, and freedom at the Lake Country Freedom 5K/10K Run, Walk & Ruck in beautiful Oconomowoc, Wisconsin! Held during the city's 151st Hometown Celebration, this family-friendly event offers something for everyone—whether you're running for a personal best, walking with friends, or rucking in honor of our service members.

    Choose between the 5K or 10K course, both showcasing scenic Lake Country views. Every participant receives a finisher’s medal, event t-shirt, and—true to American tradition—a hot dog at the finish line!

    Join us for this patriotic celebration of fitness, fun, and community spirit.

    Here's what awaits you:

    👪Family friendly

    🚶Walker friendly 2 mile option

    🧒FREE kiddos 1K

    🏃‍♀️ 5K & 10K run or Ruck options on a super flat and fast course

    🌭FREE finisher hot dogs + fixins & sides

    🏅Finisher woodles from Oconomowoc's very own Ridgeway Woodworks

    🐶Dog friendly event

    🛹Make it a day and let the kids skate at the Ocon skatepark & splash pad!

    Whether you're a seasoned runner or a casual walker, we have a distance for you!

    103 W. Jefferson Roosevelt Park (S Main & E Forest) Oconomowoc, WI US 53066
    2.1 km from Oconomowoc
    103 W. Jefferson, Oconomowoc, Wisconsin, 53066, United States
    OpenStreetMap Google Maps

    2 Miles 3.1 Miles 5k 6.2 Miles 10k 15.5 Miles Run Walk

  • Lake Country Triathlon [runsignup.com]

    Sat, Jul 25, 2026 at 6:30 AM

    Description

    Make sure you follow us on Facebook for the latest updates.

    I TRI, THEREFORE I AM! ELEVEN YEAR ANNIVERSARY!

    Join us on Saturday, July 25, 2026 for the Lake Country Triathlon, one of the Midwest...

    Make sure you follow us on Facebook for the latest updates.

    I TRI, THEREFORE I AM! ELEVEN YEAR ANNIVERSARY!

    Join us on Saturday, July 25, 2026 for the Lake Country Triathlon, one of the Midwest premiere endurance challenges. Located in the heart of beautiful Lake Country, Wisconsin. The Lake Country Triathlon offers an amazing race experience that begins with a swim in the clear waters of Lac La Belle, an incredible scenic ride through the rural glacial landscape of SE Wisconsin, and a run through the charming community of Oconomowoc.

    This year is our 11th year since re-establishing the triathlon in 2015. Over the past 11 years, we've seen athletes from nearly every state, Canada, and even Europe. We are the perfect setting for the first time triathlete and provide challenging competition for the world's best elite triathletes. We're hoping this year will be our largest and best Lake Country Tri yet and we hope you'll join us in July!

    Alan Halfen

    Race Director
    205 m from Oconomowoc
    304 W. Wisconsin Ave, Oconomowoc, Wisconsin, 53066, United States
    OpenStreetMap Google Maps

    17.65 Miles 32.7 Miles 70.3 Miles Run Swim Triathlon

  • Lake Country Half Marathon [runsignup.com]

    Sat, Aug 29, 2026 at 8:00 AM

    Description

    The ONLY race around Lac La Belle!

    8 Mile & Half Marathon Run 🏃‍♀️🏃‍♂️

    Discover the beauty of Lac La Belle 🌊 on this unforgettable 8-Mile and Half Marathon course. Starting at the Village Green in...

    The ONLY race around Lac La Belle!

    8 Mile & Half Marathon Run 🏃‍♀️🏃‍♂️

    Discover the beauty of Lac La Belle 🌊 on this unforgettable 8-Mile and Half Marathon course. Starting at the Village Green in downtown Oconomowoc 🏞, runners head north along the picturesque isthmus between Fowler Lake and Lac La Belle. The course then winds west through the charming Village of Lac La Belle 🏡, tracing the shoreline before opening into peaceful countryside roads 🌳.

    On the return, the route hugs the lake’s western edge, offering sweeping water views 🌅 all the way back to Wisconsin Avenue. The final stretch is a flat, fast push to the finish at City Beach 🏖—right on the shores of Lac La Belle.
    2.9 km from Oconomowoc
    104 E Wisconsin Ave, Oconomowoc, Wisconsin, 53066, United States
    OpenStreetMap Google Maps

    8 Miles 13.1 Miles Half Marathon Run

More races nearby →
Like Wikipedia, anyone can contribute. Sign up to add your local events.