Middlebury

Triathlon Calendar near Middlebury 2026-2027

Monthly updates for Middlebury

Get new running races (and updates) in your inbox every month.

Explore the top triathlons near Middlebury for 2026-2027! We've gathered 3 exciting races in the area. Check out our detailed list below to find your next local race.

September 2026

myTeam Triumph Triathlon

Westport | 29 mi from Middlebury

Triathlon

Family oriented triathlon at Compo Beach in Westport CT with a point to point swim, flat bike and run, age group awards and post race activities.

Family oriented triathlon at Compo Beach in Westport CT with a point to point swim, flat bike and run, age group awards and post race activities.

May 2027

BoFish Triathlon

Trumbull | 18 mi from Middlebury

Triathlon BoFish Triathlon 1 25 5 mi Relay Team 1 25 5 mi

Triathlon at Pinewood Lake with a 1 mile swim, 25 mile out and back ride, and 5 mile hilly run; proceeds benefit the Cardinal Sheehan Center.

Triathlon at Pinewood Lake with a 1 mile swim, 25 mile out and back ride, and 5 mile hilly run; proceeds benefit the Cardinal Sheehan Center.

June 2027

Pawling Triathlon

Pawling | 25 mi from Middlebury

Triathlon Pawling Triathlon 0.3 12 3.1 mi Relays 0.3 12 3.1 mi

Short-course triathlon at Lakeside Park in Pawling with a 0.3 miles swim, 12 miles bike and 3.1 miles run, plus live results and free finish line photos.

Short-course triathlon at Lakeside Park in Pawling with a 0.3 miles swim, 12 miles bike and 3.1 miles run, plus live results and free finish line photos.