15 running events in Oconomowoc, Wisconsin

The 21st running of Wisconsin’s largest running series is set to explore the inner workings of Milwaukee and its beautiful suburbs.

This series plays host to six events throughout the winter season, surrounding your favorite holidays. Bring the family to participate in the 5K or 10K. Let's Conquer the Cold!

The Pumpkin Run | Sunday, October 26 | Oconomowoc, WI

The Elf Run | Sunday, November 23 | Hales Corners, WI

Run Into The New Year | Wednesday, December 31 | Wauwatosa, WI

The Big Chill | Sunday, January 18 | South Milwaukee, WI

Cupid Shuffle | Sunday, February 15 | Shorewood, WI

Luck of the Irish | Sunday, March 15 | West Allis, WI

6 EVENT SERIES REGISTRATION BUNDLE

Join us for the 2025-2026 Winter Run Series! Start the series off with the Pumpkin Run and finish with the Luck of the Irish while completing The Elf Run, Run Into The New Year, The Big Chill, and The Cupid Shuffle in between!

**Must sign up for the 6 Event Series to earn the series medallion!

The All Access Pass is your ticket to unlimited running fun! 🏃‍♂️🏃‍♀️ One low price gives you entry into all Silver Circle Sports Events–owned races from November 1, 2025 through October 31, 2026—that’s 30+ races and over $1,000 in value. No lines, no hassle… just show up and run. 🎉

All SCSE-owned events are included, plus all brand-new 2026 events*! That’s more than 100 races on your calendar.

*Note: The Lake Country Triathlon isn’t included, but you’ll get a special discounted registration option. Client/third-party events aren’t included, but if there’s space, you may be able to jump in—just ask!

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!

2026 We are back at Lucky Chucky's!

We are all a little Irish on St. Patrick's Day and if you're like us, you prepare for St. Patrick's day all year long through a rigorous training plan, continual practice, and self sacrifice. We also run a bit so we're prepared for the Shake Your Shamrocks 5K, 10K run and 2K walk. Shake Your Shamrocks 5K, 10K run & 2K walk is part of the Wisconsin Chilly Willy Run Series.

Join Silver Circle Sports Events and the Lake Country DockHounds for the 4th Annual DockHounds Dash and Easter Egg Hunt! This one-of-a-kind race lets you experience WBC Park like never before, with a course that starts and finishes at home plate—a dream come true for runners and baseball fans alike!

Event Highlights:

✔ Home Plate Finish: Feel the excitement as you cross the finish line at home plate in WBC Park! ⚾🏁

✔ FREE DockHounds Game Ticket: All adult registrations include a FREE DockHounds game ticket! 🎟️

✔ Exclusive Swag: Celebrate your race with custom event gear and a DockHounds-themed finisher Woodle!

✔ Family-Friendly Fun: Bring the whole family—there’s something for everyone!

📧 Game Ticket Redemption: After the event, you’ll receive an email from the DockHounds with instructions on how to claim your free ticket.

Don’t miss out on this unique chance to combine your love of running with a day at the ballpark! Sign up, lace up, and let’s dash to home plate together! 🏃‍♀️⚾

Welcome to the Wisconsin Trail Assail Series! 🌲🏃‍♂️🏃‍♀️

Experience seven races over seven months—building to an epic series finale. The Wisconsin Trail Assail tours some of the most scenic routes in Waukesha County and Wisconsin State Parks, with courses for every level.

Pick your challenge each month: 5K, 10K, or Half Marathon. Run it, walk it, chase a PR, or just collect trail miles with friends—the series is proudly walker-friendly.

Why you’ll love it:

• Varied terrain and views all season long

• Consistent, well-marked courses and friendly vibes

• A series-ending championship to cap your journey

Ready to hit the dirt? Join the Wisconsin Trail Assail and stack finish lines all season.

WTA All Access Pass & Rucking!

🚀 Skip the Lines With The WTA All Access Pass! 🏃‍♂️

WTA 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 👕💰- 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 about the trails, not the lines. 🌲

Important Notice:

Your All Access Pass is non-transferable. Sharing your pass with another individual is not permitted. If someone else uses your pass, you will forfeit your access privileges.

Thank you for respecting this policy—it helps us keep the program fair for all participants.

Rucking at All Events!

Rucking is a physical activity that involves walking or hiking with a weighted backpack (called a rucksack). The term comes from the military, where soldiers train and operate carrying heavy loads over long distances. In civilian fitness and recreation, rucking is gaining popularity as a versatile and low-impact workout. We now offer it at all Wisconsin Trail Assail Events!

More information about rucking.

Series Registration:

• Select your distance during registration (5K, 10K, or Half Marathon).

• Don’t worry—you can switch distances for free at any time!

• Please note: series registrations are non-deferrable.

Single Race Registration:

Want to participate in individual events? Click on the specific race link below to register for that event.

Kiddo's 1K Registration:

Our Kiddo's Races are free! If your little one wants to join the fun, please register them for the individual Kiddo's race of your choice.

Get ready to explore the trails, challenge yourself, and have a blast with the Wisconsin Trail Assail Series! 🌲👟

🏃‍♂️ The Non-Cancelled Marathon: A Race Built to Last! 🏅

The Non-Cancelled Marathon: Fast by Design. Legendary by Nature.

Born in 2020 as a bold answer to race-day uncertainty, the Non-Cancelled Marathon has grown into a go-to event for runners hungry for PRs and Boston qualifiers.

This is not just flat. It is laser-flat, lightning-fast, and fully certified, a course built to reward strong legs and smart pacing. Even better, it is a dream for spectators. Your fans and crew can cheer you on up to eight times without budging, then roll straight into the start and finish to witness the moment you make it official.

If you are ready for a high-energy, runner-first marathon that delivers speed, support, and unforgettable vibes, lace up and join us. This is the race that shows up.

Course certification number WI21003DM.

America’s 250 Anniversary Tour is Silver Circle’s red-white-and-blue victory lap celebrating 250 years of American grit—the kind built on service, sacrifice, and showing up for your community. 🇺🇸✨

This five-race series is unapologetically patriotic: flags flying, anthem energy, and miles with meaning. Whether you’re racing for a PR, walking with family, or rucking in honor of someone who served, every event is designed to celebrate freedom and directly support those who defended it—especially our veterans and veteran-focused missions like Operation FINALLY Home (building mortgage-free homes for wounded veterans) and Stars & Stripes Honor Flight (sending veterans to Washington, D.C. to be honored). 🎖️🫶

Each stop brings its own flavor of freedom:

• Independence Day Run — start your holiday with a patriotic run/walk in the scenic Fox River Park setting. 🎆

• Lake Country Freedom 5K/10K — choose your distance, soak up the Lake Country views… and yes, there’s a classic American hot dog waiting at the finish. 🌭

• Operation FINALLY Home 5K — a fast, flat course along the Menomonee River path that invites you to run, walk, or ruck for a mission that matters. 🏃‍♀️

• Stars & Stripes Honor Run — a lakefront salute at Veterans Park, with proceeds supporting Stars and Stripes Honor Flight to help send veterans to Washington, D.C. to be honored. 🌟

• Vets Day — a meaningful late-season race at the War Memorial that honors veterans and active-duty service members. 🇺🇸🎖️

What to expect

Big energy. Bigger purpose. Patriotic touches at each stop. And a simple mission: celebrate America’s 250th by backing the people who’ve kept it standing.

Because if we’re celebrating freedom, we might as well do it the right way—together, loud, and with a finish line. 🏁🎶

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

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.

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