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4 walking events in Waukesha, Wisconsin

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

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  • Trailbreaker [runsignup.com]

    Sun, Mar 29, 2026 at 7:45 AM

    Description

    The Trailbreaker is Waukesha’s signature running event, proudly held every year since 1993. What began as the vision of three passionate local runners has grown into a celebrated tradition that...

    The Trailbreaker is Waukesha’s signature running event, proudly held every year since 1993. What began as the vision of three passionate local runners has grown into a celebrated tradition that brings the community together each spring.

    Originally featuring a Marathon, Half-Marathon, 5K Run, and 2-Mile Walk, the Trailbreaker offers something for everyone — from seasoned marathoners to families looking for a fun and active day out.

    Since 2009, the event has been hosted by the Park Foundation of Waukesha, Inc. as a fundraiser supporting the enhancement of city parks, trails, recreation programs, and Waukesha’s urban forest.

    In 2023, Silver Circle Sports Events, LLC (SCSE) partnered with the Park Foundation under a long-term agreement to manage all aspects of the Trailbreaker. This collaboration ensures the event will continue to grow while staying true to its community roots and mission.

    Whether you’re chasing a PR or just enjoying the route, the Trailbreaker is more than a race — it’s a Waukesha tradition. 🏃‍♀️🌳

    Charity Partner - Park Foundation of Waukesha

    Over $200,000 has been generated and re-invested with the Parks, Recreation, and Forestry Department to "make Waukesha a better place to live, work and play". The PFW Inc. is a 501(c)3 organization that utilizes funds raised to promote "Community Quality of Life". All staff are unpaid volunteers. Please consider making a donation!

    This event provides distances for all runners! Come join the fun and support our local parks and community!

    New for 2026 - Rucking!

    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.

    More information about rucking.

    The RAD

    🏃‍♀️ Training for a spring marathon?

    We’ve got your long run covered at the Trailbreaker!

    Introducing The RAD (Run Any Distance) — perfect for runners needing a big mileage day without the race-day pressure. You’ll get all the perks of every other distance — timing, course support, swag, snacks — just no age-group awards (for the obvious “we have no idea what distance you actually ran” reasons 😆).

    Get your long run done, enjoy the crowd energy, and maybe even earn some hot chocolate miles. ☕💪

    1.85 Miles 3.1 Miles 6.2 Miles 13.1 Miles 20 Miles 26.2 Miles Run Trail Walk

    1120 Baxter Street, Waukesha, Wisconsin, 53186, United States
    OpenStreetMap Google Maps

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