Trail Running calendar near Fairfield 2026-2027

A spring 10K trail race in Cross River NY on April 25 2027, organized by Leatherman's Loop Races. Entry is by lottery with registration Jan 8 to Jan 11 2027 and the $58 fee includes the park entry.

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 50 mile ultra, a 26.2 mile trail marathon, and relay options on the Shawangunk Ridge to raise funds for Mohonk Preserve.

Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.

A technical trail event near Beacon, NY offering a roughly 14.5 mile half and a 26.5 mile full with large elevation gain, exposed climbs, staffed aid stations, post race food, a shirt and a finisher item.

A multi-day timed running festival at the Sussex County Fairgrounds with a certified 1-mile loop, options from 6 to 144 hours plus Marathon and 50K, night lighting, central aid station, camping and electronic lap timing.

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 through Bethpage State Park featuring soft trails, live timing, free finish-line photos, and advance bib pickup at Orangetheory Fitness Farmingdale.

A technical mountain trail race in northern New Jersey offering a 50K with over 7000 ft gain plus 10 mile and 5 mile options, map requirements for the 50K, mandatory gear checks, and aid stations on the longer courses.

A community 5K in Ellenville starting and finishing at Aroma Thyme Bistro, with a course along the base of the Shawangunk Mountains and a stretch on the newly resurfaced Rail Trail. Proceeds benefit local food pantries and youth scholarship..

A trail 5K at Blydenburgh County Park in Hauppauge with on site refreshments, an in person and a virtual participation option, 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.

Point-to-point trail runs of 112 or 50 miles along the New England Trail blue blazes to Guilford, CT, requiring dedicated crews, navigation, and night trail experience.

A two distance event at Rockland Lake State Park with a flat, accessible 5K and a rugged 10K up the Long Path to Hook Mountain Summit. The 10K features 1,300 ft of elevation gain and one on course aid station.

Timed 5K trail run at Coogan Farm in Mystic CT through meadows, woods and fields, capped at 150 runners with tiered fees and youth pricing.

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 educat..

A community 5K and 1 Mile Family Walk at Camp Edey in Bayport supporting Girl Scouts of Suffolk County, featuring race amenities, free finish line photos, live results, age-group awards, and family activity stations.

A limited field multi day trail ultra in Stratford CT run on a 2.5 mile loop with focused aid at a single pavilion and invitation only entries for the 72 hours format.

Social trail runs in Edison NJ with secret start locations, 2 and 5 mile options, a post-run party, volunteer perks, and an organizer-listed waiver and hazards.

Trail hash run in Middlesex County with a 5-mile Eagle Trail and a 2-mile Turkey Group Run, plus a post-run social and volunteer benefits.