Wisconsin ×Oconomowoc × Clear all
Showing 13 of 13 races races found
NOV 1

All Access Pass

Oconomowoc, WI
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!
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NOV 8

Chilly Willy Winter Run Series - SEVEN Events!

Oconomowoc, WI
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. OsborneChief 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 acr
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APR 4

DockHounds Dash & Easter Egg Hunt

Oconomowoc, WI
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
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APR 10

Wisconsin Trail Series

Oconomowoc, WI
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 longConsistent, well-marked courses and friendly vibesA 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 ou
trail
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APR 25

The Non Cancelled Marathon

Oconomowoc, WI
🏃‍♂️ 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.
Marathon
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JUN 6

Yellow Brick Road 5K

Oconomowoc, WI
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 shirtsRace 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 down
5K
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JUN 18

Silver Circle Trivia - Ocon

Oconomowoc, WI
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.
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JUL 4

Lake Country Freedom 5K & 10K

Oconomowoc, WI
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 &#x1f
5K10K
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JUL 25

Lake Country Triathlon

Oconomowoc, WI
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
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AUG 29

Lake Country Half Marathon

Oconomowoc, WI
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.
Half Marathon
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SEP 12

DoLittle Marathon

Oconomowoc, WI
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.
Marathon
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OCT 10

Zachariah's Acres Fall Run, Walk & Roll

Oconomowoc, WI
All proceeds benefit children with special needs at Zachariah's Acres, a 501(c)(3) organization located in the town of Oconomowoc, WI.    Zachariah's Acres hosts nature-based experiences for children with special needs and their families. When families attend one of our signature events, they create life-long memories, enhance social skills, strengthen family relationships, and simply relax in nature. Favorite activities include fishing, guided nature walks and rolls through prairie grass and wildflowers, snowshoeing, sleigh rides, hay wagon rides, apple picking, or cooking in our educational kitchen. More than 38 schools, nonprofits, and community partners visit Zachariah's Acres on a regular basis for educational field trips, outdoor recreation, vocational skills training, volunteer opportunities, and hands-on learning.  For more information & to get involved, visit zachariahsacres.org. New for 2026 - Rucking! What is rucking? Rucking is a physical activity that invol
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OCT 29

OPEF Trick or Trot

Oconomowoc, WI
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!
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