Sleepy Hollow
Triathlon Calendar near Sleepy Hollow 2026-2027
Monthly updates for Sleepy Hollow
Get new running races (and updates) in your inbox every month.
Explore the top triathlons near Sleepy Hollow for 2026-2027! We've gathered 12 exciting races in the area. Check out our detailed list below to find your next local race.
August 2026
A multi-event weekend at Theodore Roosevelt Memorial Park featuring a main triathlon with a 1/2 mile swim, 12.3K bike loop and 5K run, plus relay, AquaBike, BikeRun and two junior race distances.
A Central Park duathlon on August 23 featuring two 2.2 mile runs and a 12 mile bike over two loops of the Park Drive, with an individual race and a team relay for two to three athletes.
September 2026
A weekend of TOUGHMAN multisport championships at Lake Welch Beach in Stony Point, NY, featuring long course, Olympic, duathlon, aquabike, relay, collegiate, and youth races with age and cutoff rules.
At Rockaway Beach competitors swim in open Atlantic water, bike two flat six mile loops on the boardwalk, and finish with an out and back 3 mile run along the boardwalk. Relay and aquabike options are offered and no USAT license is required.
TOUGHMAN Westchester at Rye Playland on September 19 to 20, 2026 features Olympic triathlon, aquabike, duathlon, an open water mile swim and youth triathlon events. Olympic distances include a 1.5 km swim, 40 km bike and 10 km run.
Monthly updates for Sleepy Hollow
Get new running races (and updates) in your inbox every month.
Sea Cliff Triathlon on 09/19/2026 takes place at Harry Tappen Beach and offers individual, youth, and several relay formats with swim, bike, and run legs and specified team rules and fees.
Sprint triathlon, relay teams, and a family-friendly 5K around Lake Mahopac on 19 September 2026, with proceeds supporting a young investigator fund at New York-Presbyterian Weill Cornell.
Triathlon and duathlon at Lake Welch in Harriman State Park on September 20, 2026 featuring a 0.5 mi swim, 15 mi bike loop, and 2 mi run with medals and age awards.
A community triathlon at Compo Beach on September 27, 2026 with a point to point swim, flat neighborhood bike and run courses, awards and post race activities.
October 2026
Run and bike around Central Park with an optional team boat relay that adds a rowing loop on the Lake after the bike segment.
A Manhattan triathlon on October 10, 2026, with a Hudson River swim and a finish in Central Park. Formats include sprint, Olympic, aquabike options and relays; the event is USAT sanctioned and welcomes para-athletes.
November 2026
A fall duathlon in Prospect Park featuring a 2.1 mile opening run, a 10 mile three-lap bike, and a 3.3 mile final loop with about 140 ft of climbing. Post race barbecue and volunteer opportunities are available.