Darien
Trail Running Calendar near Darien 2026-2027
Explore the top trail runs near Darien for 2026-2027! We've gathered 51 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
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.
A trail 5K at Bethpage State Park with a free kiddie run, virtual option, post-race refreshments, and age-group recognition.
A 6 hour trail ultra at Roosevelt Forest in Stratford CT with a 2.3 mile loop, on-course food and hydration, a 50 person field, and podium awards for top men and women.
April 2027
A trail 5K with a free kiddie run at Bethpage State Park, refreshments and a virtual entry option; 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 and walk at Blydenburgh County Park with a mixed-surface course, dog-friendly rules, on-site amenities, and proceeds supporting Last Chance Animal Rescue.
A community 5K running event in Woodhaven, NY on April 10, 2027 supporting Jamaica College and its Penn Relays Team; registration fee $20.
A scenic all-terrain 5K and a 0.3 mile kids fun run at Stamford Museum and Nature Center on April 11, 2027, with farm views and a free kids educational dropoff.
Point-to-point 50K and 25K across the Suffolk County Greenbelt Trail from Sunken Meadow to Heckscher State Park, featuring five aid stations and shuttle service.
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 spring trail event in Cross River NY, Leatherman's Loop is a 10K lottery-entry race with 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 5K run and walk at Bethpage State Park with winding soft trails, live timing, free finish line photos, and awards for top male and female overall.
A community 5K trail run and walk at Blydenburgh County Park with on-site amenities, a virtual option, and donations 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.