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Date:
Fri, Apr 10, 2026 at 9:00 AM – 11:00 AM
Location:
1327 Wall Street
Oconomowoc, Wisconsin
53066
United States
OpenStreetMap Google Maps
Links:
runsignup.com
Tags:
13.1 Miles Run Trail Walk

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! 🌲👟


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 →
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