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. 🏃♀️🌳
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!
Apr 04, 2027
Distance — Kiddos 1K
Type — Running
07:45
$0.00
Apr 04, 2027
Distance — 13.1 Miles
Type — Running
08:00
$50.00
Apr 04, 2027
Distance — 13.1 Miles
Type — Running
08:00
$50.00
Apr 04, 2027
Distance — 26.2 Miles
Type — Running
08:00
$70.00
Apr 04, 2027
Distance — 20 Miles
Type — Running
08:00
$70.00
Apr 04, 2027
Distance — 6.2 Miles
Type — Running
08:15
$32.50
Apr 04, 2027
Distance — 6.2 Miles
Type — Running
08:15
$32.50
Apr 04, 2027
Distance — 3.1 Miles
Type — Running
08:15
$32.50
Apr 04, 2027
Distance — 3.1 Miles
Type — Running
08:15
$32.50
Apr 04, 2027
Distance — 1.85 Miles
Type — Running
08:15
$32.50
These values represent the 3-year monthly averages for April in Waukesha.
Learn more about the host city, Waukesha.
Waukesha is a city of 62,000 people (2021) in Southeast Wisconsin. It is about 20 miles west of downtown Milwaukee.
Read more launchTours and activities near Waukesha, powered by Viator.
Watch highlights and course previews from previous years.
Read what other athletes have to say about their experience at the Trailbreaker.
Be the first to share your experience with the community!
Spotted an error or missing detail about the Trailbreaker? Help us improve.
Explore other exciting events happening in this same region.
location_on Oconomowoc, Wisconsin, US
calendar_today Oct 10, 2026
Hand-picked events we think you’ll love.
Oct 03, 2026
Join Ohio American water Works Association (OAWWA) to raise funds for Water for People, a nonprofit organization with a…
Read more
Oct 03, 2026
Registration/Check-in begins at 7:00 am. The run will begin promptly at 8:00 am. Overview Howe2Run is hosting a Fun Run…
Read more
Oct 03, 2026
The Waterman’s Triathlons are nestled on the Eastern Shore of Maryland in picturesque Rock Hall, MD. Just 18 miles from…
Read more
Oct 03, 2026
The River Run for the Roots is an annual 5K run/walk from the Common Roots Brewery to benefit its nonprofit, the Common…
Read more
