What is the Trailbreaker?

The Trailbreaker is Waukesha’s signature running event, held annually since 1993. Originally created by three local runners, it has grown into a major fundraiser managed by the Park Foundation of Waukesha, Inc. Since 2009, the event has supported the enhancement of city parks, trails, recreation programs, and the urban forest. In 2023, Silver Circle Sports Events, LLC (SCSE) partnered with the Foundation to manage event operations, ensuring continued community impact. Over $200,000 has been raised and reinvested into Waukesha’s recreational infrastructure.

What distances are available for this event?

• →Marathon starting at 8:00 AM CDT
• →Half Marathon starting at 8:00 AM CDT
• →10K starting at 8:15 AM CDT
• →5K starting at 8:15 AM CDT

What are the new rucking divisions for 2026?

• →Half Marathon Ruck starting at 8:00 AM CDT
• →10K Ruck starting at 8:15 AM CDT
• →5K Ruck starting at 8:15 AM CDT

How much does registration cost?

• →Marathon: $80 (increases after March 27, 2026, at 11:59 PM CDT)
• →Half Marathon: $70 (increases after March 27, 2026, at 11:59 PM CDT)
• →10K: $45 (increases after March 27, 2026, at 11:59 PM CDT)
• →5K: $45 (increases after March 27, 2026, at 11:59 PM CDT)
• →Half Marathon Ruck: $67.50 (increases after March 27, 2026, at 11:59 PM CDT)
• →10K Ruck: $45 (increases after March 27, 2026, at 11:59 PM CDT)
• →5K Ruck: $45 (increases after March 27, 2026, at 11:59 PM CDT)

What is the schedule for the event?

• →Marathon and Half Marathon start at 8:00 AM CDT
• →10K and 5K start at 8:15 AM CDT
• →Half Marathon Ruck and 10K Ruck start at 8:00 AM CDT
• →5K Ruck starts at 8:15 AM CDT

What can participants expect in terms of course terrain?

The Trailbreaker features a mixed-terrain course that includes packed dirt trails, grassy park paths, and some paved connectors or road sections depending on the specific loop design. The course is designed to showcase Waukesha’s urban forest and city parks, offering a blend of natural and urban landscapes. The route is known for being runner-friendly but challenging, with rolling hills typical of the Southeast Wisconsin park trails.

What is rucking and how does it work?

Rucking is a form of walking or hiking with a weighted backpack, known as a rucksack. It is a low-impact workout that draws from military training principles. The Trailbreaker introduces rucking divisions for the first time in 2026, allowing participants to complete the half marathon, 10K, and 5K distances while carrying a weighted backpack. This addition expands the event’s appeal to a broader range of participants, including those interested in fitness and military-inspired challenges.

What is included in registration?

Registration for the Trailbreaker includes access to the event course, timing, and support along the route. Participants will also receive a race bib, a finisher’s medal, and a race shirt. Additional details about what is included with each race distance may be available on the event website, though specific course maps and GPX files are recommended to be searched for directly.

What is the expected weather on the event day?

On Sunday, March 29, 2026, in Waukesha, the expected weather is likely to be mild, with temperatures ranging between 40°F and 55°F (4°C to 13°C). The forecast suggests mostly cloudy conditions, with little to no precipitation. These conditions make for ideal running weather, allowing participants to enjoy the course without extreme heat or cold.

How does the Trailbreaker support the community?

The Trailbreaker is managed by the Park Foundation of Waukesha, Inc., and has raised over $200,000 since its inception. The funds generated from the event are reinvested into the community to enhance city parks, trails, recreation programs, and the urban forest. By supporting the event, participants contribute to the preservation and improvement of Waukesha’s natural and recreational resources.

Are there any special features or highlights of the 2026 event?

The 2026 Trailbreaker introduces rucking divisions, marking a new and exciting addition to the event. This allows participants to engage in a unique form of physical activity that combines endurance with strength training. The event continues to focus on Waukesha’s park systems, offering a scenic and challenging route that aligns with its mission to promote community quality of life. The event also maintains its inclusive approach, welcoming runners and ruckers of all skill levels.