5 events in Waukesha, Wisconsin

Spring is here, and it's the perfect time to dust off your running shoes! Shake off the winter hibernation and join us for the First Call 5K, 10K, and Half Marathon. This is your chance to set the tone for an incredible 2026 race season. This year’s race takes place on the lightning-fast Glacial Drumlin and Fox River Trails—so fast, it’s faster than flat! Don’t miss out—The First Call is part of the exciting Chilly Willy Winter Run Series.

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. ☕💪

Wisconsin Trail Assail Wrap Party & Chilly Willy Winter Run Series Kickoff 🎉🏃‍♂️🍻

Join Silver Circle Sports Events, LLC and Raised Grain Brewing Co. for an exciting celebration as we wrap up the Wisconsin Trail Assail and kick off the Chilly Willy Winter Series at Raised Grain Brewing Co. 🍺🎉 Hey! There is also Silver Circle Trivia!

This event is free, but we kindly ask that you register in advance to help us manage capacity. Feel free to bring a friend and enjoy a fun evening with fellow runners! 👟🙌

If you’d like to make a donation during registration to Silver Circle Foundation, Inc. (501(c)(3)), your support would be greatly appreciated. ❤️🙏

We look forward to celebrating with you! 🎊