Chilly Willy Winter Run Series - SEVEN Events!

More races nearby

• Wisconsin Trail Series [runsignup.com]

  Fri, Apr 10, 2026 at 9:00 AM

  Description

  ▼ Show more Show less

  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! 🌲👟

  ---

  0 m from Oconomowoc
  1327 Wall Street, Oconomowoc, Wisconsin, 53066, United States
  OpenStreetMap Google Maps

  13.1 Miles Run Trail Walk

• The Non Cancelled Marathon [runsignup.com]

  Sat, Apr 25, 2026 at 8:00 AM

  Description

  ▼ Show more Show less

  🏃‍♂️ 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.

  2.3 km from Oconomowoc
  600 S. Main Street, Oconomowoc, Wisconsin, 53066, United States
  OpenStreetMap Google Maps

  3.1 Miles 6.2 Miles 13.1 Miles 26.2 Miles Marathon Run

• Guzi's Hunt for the Cure Run/Walk [runsignup.com]

  Sun, May 17, 2026 at 10:00 AM

  Description

  ▼ Show more Show less

  We are thrilled to announce the 6th Annual Guzi’s Hunt for the Cure Run/Walk for Huntington’s Disease, taking place on Sunday, May 17, 2026, at Oak Creek’s Lake Vista Park. Thanks to the incredible...

  We are thrilled to announce the 6th Annual Guzi’s Hunt for the Cure Run/Walk for Huntington’s Disease, taking place on Sunday, May 17, 2026, at Oak Creek’s Lake Vista Park. Thanks to the incredible support from our sponsors, participants, and generous donors, we have raised over $380,000 in the past five years for the Huntington’s Disease Society of America (HDSA) – Wisconsin Chapter and Guzi’s Hunt For The Cure Foundation, Inc. This year, we aim to continue this momentum and achieve our fundraising goal of $75,000.

  About Chris Guzikowski and Huntington’s Disease

  In 2020, Chris Guzikowski, a lifelong resident of Oak Creek, 6th District Alderman, member of the Oak Creek Lions, and 2018 Oak Creek Citizen of the Year, received a life-altering diagnosis of Huntington’s Disease (HD). This rare genetic neurological disorder affects approximately 41,000 individuals in the U.S. and has no cure. HD manifests as ALS, Parkinson’s, and Alzheimer’s, simultaneously, leading to cognitive decline, involuntary movements, irritability, balance issues, and ultimately, swallowing difficulties and death. The hereditary nature of HD means that Chris’s three daughters also face a 50% chance of inheriting this devastating condition. In 2021, Chris and his family launched Guzi’s Hunt for the Cure 5K Run/Walk to raise awareness and funds for HD research and support, with the ultimate goal of eradicating Huntington’s disease.

  A Personal Journey with Huntington’s Disease

  In 2023, as Chris’s daughter Carley Renner and her husband Nate were preparing to start their family, they received the heartbreaking news that Carley also carries the Huntington’s gene. This not only means Carley faces the same fate as her father but also that any biological children they have would face a 50% chance of inheriting the gene. Fortunately, they received a grant for high-cost fertility assistance, allowing them to ensure their biological children would be HD-free. They have since welcomed two healthy HD-free children! Inspired by this blessing, Carley and Nate established Guzi’s Hunt for the Cure Foundation, Inc., which provides financial support (grants) to couples impacted by Huntington's Disease through fundraising, donations, and sponsorships.

  Guzi’s Hunt for the Cure Foundation, Inc.

  The foundation is dedicated to raising awareness about Huntington’s Disease and the benefits of pre-implantation genetic testing with IVF. We are excited to announce the Khoury family welcomed a healthy baby boy in 2025. Continuing this momentum, the foundation recently awarded its third grant to a deserving couple. A single PGT-IVF journey can carry costs of $35,000+. The proceeds from this year’s fundraising efforts will support both Guzi’s Hunt for the Cure Foundation, Inc. and HDSA- WI Chapter.

  We sincerely appreciate your consideration in supporting our mission to reach our 2026 fundraising goal of $75,000. We hope to see you at Guzi’s Hunt for the Cure 5K Run/Walk for Huntington’s Disease on Sunday, May 17th!

  9.8 km from Oconomowoc
  4001 Lake Vista Parkway, Jefferson County, Wisconsin, 53154, United States
  OpenStreetMap Google Maps

  5k Run Walk

• America's 250th Tour [runsignup.com]

  Sat, May 23, 2026 at 9:00 AM

  Description

  ▼ Show more Show less

  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. 🏁🎶

  ---

  2.3 km from Oconomowoc
  1776 Street, Oconomowoc, Wisconsin, 53066, United States
  OpenStreetMap Google Maps

  3.1 Miles Run Walk

• Yellow Brick Road 5K [runsignup.com]

  Sat, Jun 06, 2026 at 7:45 AM

  Description

  ▼ Show more Show less

  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