Trailbreaker

Trailbreaker Overview

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.

• Event Types: Originally featuring a Marathon, Half-Marathon, 5K Run, and 2-Mile Walk.
• All Abilities: The Trailbreaker offers something for everyone — from seasoned marathoners to families looking for a fun and active day out.
• Charity Support: Since 2009, the event has been hosted by the Park Foundation of Waukesha, Inc.
• Community Focus: The event supports the enhancement of city parks, trails, recreation programs, and Waukesha’s urban forest.

2023 Partnership

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.

• Growth Assurance: This collaboration ensures the event will continue to grow.
• Mission Focus: Staying true to its community roots and mission.
• Experience: Whether you’re chasing a PR or just enjoying the route.
• Tradition: 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.

• Donation: Please consider making a donation!
• Distances: This event provides distances for all runners!
• Community Support: 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.

• Gaining Popularity: In civilian fitness and recreation, rucking is gaining popularity as a versatile and low-impact workout.
• Further Reading: More information about rucking.

The RAD

Training for a spring marathon? We’ve got your long run covered at the Trailbreaker!

• Long Run: Introducing The RAD (Run Any Distance) — perfect for runners needing a big mileage day without the race-day pressure.
• Event Perks: You’ll get all the perks of every other distance — timing, course support, swag, snacks.
• No Awards: Just no age-group awards (for the obvious “we have no idea what distance you actually ran” reasons).
• Enjoy the Energy: Get your long run done, enjoy the crowd energy, and maybe even earn some hot chocolate miles.