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.
October 2026
A timed trail 5K at a private 150-acre farm in Wilton CT with an accessible short run, live music, food, and proceeds supporting The Prospector.
A scenic October 5K on the carriage roads of Rockefeller State Park Preserve with hilly terrain, awards, and proceeds supporting carriage road maintenance.
Trail half marathon in New Rochelle running a single loop through five Westchester parks on mostly dirt shaded trails with frequent wildlife on October 11, 2026.
Trail 5K run/walk at Blydenburgh County Park on October 11, 2026 with in-person and virtual options, a participant shirt, shaded trails, and age-group recognition.
Trail running at Muscoot Farm with a 5 mile race and two kids races on October 25, 2026 in Katonah, NY.
Trail half marathon and 5K in the Hudson Highlands with a kids costume run and aid stations for the half.
November 2026
Experience a community-focused trail race featuring a 4 mile loop of rolling farm trails and single track with timed options, a 4 mile distance, and a 5K Canicross.
A community 72nd anniversary event in Lake Ronkonkoma with a timed 5K run/walk and an untimed fun run on mixed pavement, grass and trail surfaces.
A 4K grass cross country event at the Northport VA Golf Course with military and youth categories, a short fun run, awards, and proceeds supporting local veterans.
Timed laps at New Canaan High School Track where adults run for 14 minutes and 48 seconds and kids run one 400 m lap, with proceeds supporting the Ram Council Foundation.
A trail 10k at Ward Pound Ridge Reservation on November 8, 2026 plus a monthlong November Raven 100k Challenge with a wooden finisher medallion.
USATF Long Island 8K Open and Masters Para Athletic XC Championships on November 8 2026 at Bethpage State Park Playground in Bethpage NY
A family 5K trail run and virtual option at Bethpage State Park on November 14, 2026 with a free kiddie dash, post-race refreshments, and proceeds supporting the Never Stop Running Foundation.
Inaugural backyard ultra at Cranbury Park in Norwalk on November 14 with repeated 4.167 mile loops, alternating loop direction every four hours.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.
A memorial 5K run and walk on the cross country course in Danbury offering a chance for friends, family and teammates to gather and remember.
A farm based 5K trail run plus a kids fun run for ages 6 and under in Yorktown Heights supporting Friends of Hilltop Hanover Farm.