The Outdoorsman Triathlon is the nation's oldest continuous triathlon and consists of a 1 mile swim, 4 mile run and an 8 mile paddle down the Little Tennessee River. Individual competition is held on Saturday and relays are held on Sunday.

In 1976 outdoorsman Payson Kennedy (founder of the Nantahala Outdoor Center), Olympic canoeist John Burton, and Georgia Tech professor Russ Callen issued a challenge to athletes to come battle the raw elements of the Great Smoky Mountains in an outdoorsman's triathlon. This race even has in the rules that "assistance with changing clothes, putting on shoes, or supplying food or drink to competitors is prohibited. Competitors are on their own once they begin the race and can only receive assistance from race officials". The rules governing the running section state "no form of locomotion other than running, walking, or crawling is allowed". A news article in Triathlon Today concerning the Outdoorsman Triathlon stated that had these competitors been around 200 years ago "these mountains and gaps would now bear their names".

Paddler Magazine described the event as one of the nation's top multisport races.

Today the Outdoorsman Triathlon is the oldest continuously running triathlon in the United States and has seen Olympic gold medal athletes, World Champion athletes, and three generations of family participants. The event is sponsored by The Outdoorsman Triathlon Charitable Trust, First Citizens Bank of Bryson City, Rolling Thunder River Company, Nantahala Outdoor Center, Nantahala Village, Russ Callen, Dodge Havens, and Scott Dillery.

On Sunday, college athletes from around the country compete in the First Citizens Bank Collegiate Challenge Relay Race. This class is open to full-time college students (each team must have at least one women member) and the top three teams are awarded cash prizes to be donated to the college club of their choice. There are numerous spectator spots for viewing the race. The swim course is in a cove next to the Route 28 bridge and the run course travels past the church at the top of Needmore Road Hill. The canoe segment down the Little Tennessee can be viewed at the Swinging Bridge or the Route 19 bridge.

The race is always held on the last full weekend in September. The 40th Annual Outdoorsman Triathlon will take place September 26-27, 2015.