Darien
Trail Running Calendar near Darien 2026-2027
Explore the top trail runs near Darien for 2026-2027! We've gathered 58 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
March 2027
A 5K trail run and free kiddie clover fun run at Bethpage State Park with a virtual option, finisher shirts, post race refreshments and age group awards.
April 2027
A scenic 5K at Bethpage State Park with in person and virtual options, refreshments, bib mailing, and age-group recognition; proceeds support the Never Stop Running Foundation.
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/walk at Blydenburgh County Park in Smithtown, NY, featuring mixed trail surfaces, dog-friendly rules, on-site amenities and proceeds benefiting Last Chance Animal Rescue.
Point-to-point trail runs of 50K and 25K across the Suffolk County Greenbelt Trail, finishing at Heckscher State Park on April 17, 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.
A 5K run/walk at Bethpage State Park with soft trails, live results, free finish line photos, and early bib pickup at Orangetheory Fitness Farmingdale.
A 5K trail run and walk at Blydenburgh County Park supporting the Never Stop Running Foundation, with on-site refreshments, parking options, and a virtual participation choice.
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.