New Canaan
Trail Running Calendar near New Canaan 2026-2027
Explore the top trail runs near New Canaan for 2026-2027! We've gathered 47 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Community Thanksgiving event at Somers High School with a 5K and 1-mile fun run, shirts, medals, age-group awards, and scheduled packet pickup days.
Post-Thanksgiving community races at Darien High School featuring a 5K and a 1 Mile walk/run with proceeds benefiting The Depot youth center.
A trail 5K run and walk at Bethpage State Park on Nov 28, 2026 with a virtual option, a free kiddie dash, event shirts, and postfinish refreshments.
December 2026
A backyard ultra at Blydenburgh County Park: runners repeat a 4.167 mile loop each hour until one completes the final loop; proceeds support Long Island trail maintenance.
A 5K race at Van Cortlandt Park on December 12, 2026, with tiered registration pricing, bib pickup at the Tortoise and Hare Statue, T shirts and bag check.
A 5 mile winter trail race at Mountain Lakes Park in North Salem NY with start and finish in the Yurt Village, a central firepit, and proceeds supporting park trail projects.
Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.
March 2027
Trail events at Sunken Meadow State Park on a roughly 1.4 mile loop with one hour and three hour formats awarding titles for greatest distance covered.
Six hour timed trail event at Roosevelt Forest in Stratford CT with a 2.3 mile loop, a 50K option, limited field and awards for top mileage.
A trail 5K and free kiddie fun run at Bethpage State Park with a lucky shirt, postrace refreshments including beer for 21 plus, and a virtual participation option.
April 2027
A 5K trail run and free kiddie run at Bethpage State Park with a virtual option, refreshments, bib mailing, and age group awards supporting the Never Stop Running Foundation.
Mountain trail races at Bear Mountain on April 3, 2027 offering 13.1 mile, 10K and 10K ruck on rugged technical singletrack with significant elevation gain.
A community trail event in Cross River, NY featuring a 5k trail race, a 4k walk on the same trails, and a 200 meter kids dash on the contest track.
A 5K trail run and walk at Blydenburgh County Park in Smithtown supporting Last Chance Animal Rescue, with varied trail surfaces, facilities, and dog friendly rules.
Youth trail run at Katonah Memorial Park for ages 4 to 16 with 0.5 mile and 1 mile options; registration opens January 31, 2027.
A USATF sanctioned 10K trail race in Cross River, NY on April 25, 2027, with entry by lottery and a $58 fee that includes park entry.
May 2027
VCP 50K is a looped trail ultramarathon in Van Cortlandt Park on 01 May 2027. The 50K course starts with a flats lap then ten cross country loops, with stocked aid stations, drop bag access, finisher medal, singlet, meal and beer.
A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.