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.
May 2027
A 5K run and walk at Bethpage State Park with live results, free finish line photos, soft trail terrain and awards for top overall finishers.
A 5K trail run and walk at Blydenburgh County Park with in-person and virtual options, refreshments, and proceeds benefiting the Never Stop Running Foundation.
A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.
June 2027
Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being reconstructed. Proceeds support Friends of the Fire Tower for accessibility and educational impr..
August 2027
A multi-day August 2027 event at Sacred Heart University with 90 minute stair climb and walk challenges plus a five day virtual step challenge supporting Homes for the Brave.
A 17 mile trail race at State Line Lookout in Closter NJ featuring four mile technical loops, rock scrambles, stocked aid stations and significant elevation with serious hazards.