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
Hotels Near This Race
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Race Travel Insurance
Don't forget travel insurance for April 4.
You've trained for months and booked a trip to Waukesha, WI.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
