Jailbreak Triathlon

SEP
19
2026
Partner with a friend for a unique triathlon featuring canoeing on the Duck River followed by mountain biking and trail running through Chickasaw Trace County Park.
Sat 19 Sep 2026
Trail Run Canoe Mountain Bike

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Jailbreak Triathlon

The Jailbreak Triathlon is a multi-sport event organized by the Columbia Cycling Club, which has hosted the competition since 2002. Held annually in September and based in Columbia, the race begins near the Duck River below the Maury County Jail. Participants navigate a course that involves canoeing, mountain biking, and trail running through Chickasaw Trace County Park.

The race utilizes a duo format where participants must compete with a partner. Entrants can choose between two participation styles. In the Team category, both partners complete the full course; while they canoe together, their individual times for the cycling and running portions are added together for a combined result. In the Relay category, partners canoe together, but then split the remaining disciplines, with one person cycling and the other running.

The event consists of three distinct segments:

  • 3.5 Mile Canoe: Navigated on the Duck River using provided two-person canoes.
  • 7.5 Mile Mountain Bike: A single-track course through woods with technical sections and climbs.
  • 2.65 Mile Trail Run: A route primarily on flatter terrain including an area known as the "Death Ditch."

Check-in takes place at the Hanson Shelter at Chickasaw Trace Park. Because the bike segment features technical single-track trails, mountain bike experience is required. Helmets are mandatory for the cycling portion, and life jackets must be worn during the river segment. All canoes, paddles, and life jackets are provided as part of the entry fee, and personal canoes are not permitted. Visit the organization's website for the most recent information.

4 mi
Canoe
3 mi
Trail Run
Mountain Bike