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. ☕💪