15 running, walking, and triathlon events in Oconomowoc, Wisconsin

From big races to Saturday morning group runs—find running, walking, and triathlon events and connect with the local endurance sports community.

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Winter Run Series™ [runsignup.com]
Sun, Oct 26, 2025 at 9:00 AM

Description

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,...

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!

Run
Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
All Access Pass [runsignup.com]
Sat, Nov 01, 2025 at 8:00 AM

Description

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,...

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!

13.1 Miles Run Triathlon
Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
Chilly Willy Winter Run Series - SEVEN Events! [runsignup.com]
Sat, Nov 08, 2025 at 9:00 AM
Description
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...
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!
3.12 Miles 6.2 Miles 13.1 Miles Run Walk
1327 Wall Street, Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
Shake Your Shamrocks [runsignup.com]
Sat, Mar 14, 2026 at 8:45 AM

Description

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...

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.

2 Miles 3.1 Miles 6.2 Miles Run Walk
Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
DockHounds Dash & Easter Egg Hunt [runsignup.com]
Sat, Apr 04, 2026 at 8:45 AM

Description

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...

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! 🏃‍♀️⚾

2 Miles 3.1 Miles Run
Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps

Wisconsin Trail Series [runsignup.com]
Fri, Apr 10, 2026 at 9:00 AM
Description
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...
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! 🌲👟
13.1 Miles Run Trail Walk
1327 Wall Street, Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
The Non Cancelled Marathon [runsignup.com]
Sat, Apr 25, 2026 at 8:00 AM

Description

🏃‍♂️ 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...

🏃‍♂️ 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.

3.1 Miles 6.2 Miles 13.1 Miles 26.2 Miles Marathon Run
600 S. Main Street, Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
America's 250th Tour [runsignup.com]
Sat, May 23, 2026 at 9:00 AM
Description
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. 🇺🇸✨...
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. 🏁🎶
3.1 Miles Run Walk
1776 Street, Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
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 Miles 3.1 Miles 5k Run Walk
174 E., Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
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.
Run
104 E Wisconsin Ave, Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
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 Miles 3.1 Miles 5k 6.2 Miles 10k 15.5 Miles Run Walk
103 W. Jefferson, Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
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

17.65 Miles 32.7 Miles 70.3 Miles Run Swim Triathlon
304 W. Wisconsin Ave, Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
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.

8 Miles 13.1 Miles Half Marathon Run
104 E Wisconsin Ave, Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
DoLittle Marathon [runsignup.com]
Sat, Sep 12, 2026 at 7:00 AM

Description

Whether you’re gearing up for your first race, locking in a training run for a big fall marathon, or just want to cruise a gorgeous course, the DoLittle won’t disappoint. This stretch of the trail is...

Whether you’re gearing up for your first race, locking in a training run for a big fall marathon, or just want to cruise a gorgeous course, the DoLittle won’t disappoint. This stretch of the trail is scenic, smooth, and speedy — ideal for setting a PR or just enjoying the spring vibes.

🤔 What’s with the name?

You know... Do a little marathon. 😉 Whether that’s a few miles or the full 26.2, we’re here for it!

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.

3.1 Miles 6.2 Miles 13.1 Miles 24 Miles 26.2 Miles Marathon Run Trail
Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
OPEF Trick or Trot [runsignup.com]
Thu, Oct 29, 2026 at 4:30 PM

Description

Join the Oconomowoc Public Education Foundation (OPEF) for a 1-mile or 2-mile run to support our schools! This fall, OPEF is striving to raise at least $25,000 to fund new gymnastics equipment for...

Join the Oconomowoc Public Education Foundation (OPEF) for a 1-mile or 2-mile run to support our schools! This fall, OPEF is striving to raise at least $25,000 to fund new gymnastics equipment for the elementary schools, sound system improvements at the middle school, and more!

OPEF is a collaborative partner of the Oconomowoc Area School District (OASD). OPEF raises and provides funds for innovative educational opportunities and experiences not funded in the core school district budget – including classroom grants, facilities improvements, and innovative curriculum. OPEF has given more than $500,000 to the OASD in the past 18 years. Help OPEF continue the legacy of gifts from the community…to the schools…for our future!

Wear your OPEF Trick or Trot shirt, your school swag, or your Halloween costume for this fun after-school event that will have music, costumes, candy, and prizes!

Run
Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps

Local Clubs & Organizations

Barn Racing Team Club

[barnracingteam.com] [member.usatriathlon.org]
Triathlon

Contact: barnracingteam2022@gmail.com
W354S2980 Manor, House Ct, Oconomowoc, Wisconsin, 53066, United States
OpenStreetMap Google Maps
Phone: (262) 391-0517

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