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Trailbreaker

📍 Waukesha, WI
Date
Sunday, March 29, 2026
Distance
Various
Region
Waukesha
Est. Participants
Not specified
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
trail