Stamford
Trail Running Calendar near Stamford 2026-2027
Explore the top trail runs near Stamford 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.
April 2027
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 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 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..
July 2027
LIC Wellness Fest Hurricane Fit Race in Long Island City features a one block, 20-obstacle course with live results, finish line photos, wellness activities, and cash awards.
August 2027
A 5K held inside Yankee Stadium on August 8, 2027 with in-person and virtual options, chip timing, and a race medal and shirt for participants.
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.
September 2027
Six hour endurance run and relay at Belmont Lake State Park on a scenic 2.50 mile loop with team divisions, awards, commemorative shirts, and charity support.
A community 5K run and walk in Forest Park, Queens with a free 1K kids run, participant T shirts, medals, and same day results and photos.
A single-loop trail half marathon through five Westchester parks, mostly on dirt and roots, chip-timed with three aid stations and a 3 hour course limit.
October 2027
A scenic trail 5K at Blydenburgh Park with a free Kiddie Dash, on-site refreshments and a virtual entry option allowing one week to submit results.
A community 5K Run/Walk in Massapequa Park with a mixed road and trail course, finisher medals, live results, photos, and awards across many age groups.