Jailbreak Triathlon 2026

The Jailbreak Triathlon takes participants through Chickasaw Trace Park in Columbia, Tennessee. The Columbia Cycling Club manages the park's bike trails, which are frequented by local cyclists. This is a yearly, limited-entry triathlon that maintains a local-club atmosphere, having been held for 19 years. The park features 9 miles of bike trails, giving the race a more off-road character than a standard road triathlon. One past event included 88 participants. Following a COVID-related cancellation, the event resumed with organizers noting sustained participant interest. Duane Leach of the Columbia Cycling Club described the riding as "some of the best riding anywhere," calling the trails a hidden gem that merits a visit.