The Trailbreaker is an annual running event in Waukesha, organized by the Park Foundation of Waukesha, Inc., and Silver Circle Sports Events, LLC. It includes various race formats suitable for experienced runners and families alike. Since inception, it has served as a community fundraiser to support local parks, trails, and urban forestry. The event emphasizes community engagement and fitness, offering activities like rucking, a form of weighted walking. Additionally, the “Run Any Distance” option is available for flexible participation. The Trailbreaker fosters community spirit and contributes significantly to Waukesha's quality of life initiatives.