Trail Running calendar near Stamford 2026-2027

A 50K ultramarathon at Van Cortlandt Park on 05/02/2026 composed of an opening flats lap and ten cross country loops, with stocked aid station access and drop bags. Finishers receive a medal, singlet, hot meal and cold beer.

Trail event at Greig Farm in Red Hook, NY featuring 5K and 10K trail runs plus a 5K walk through meadows, orchards, and forest, with cash prizes for the top three overall male and female finishers in the 5K and 10K.

Rock The Ridge is a fundraising trail event at Mohonk Preserve on May 2, 2026. Options include a 50 mile ultra, a 26.2 mile trail marathon and relay teams, with proceeds supporting conservation and education.

Trail races at Bear Mountain State Park on May 2, 2026 include 10K, half marathon and 50K over singletrack with technical sections, rolling climbs, tree cover, rocky and muddy terrain and occasional stream crossings.

Run a flat one mile course in Van Cortlandt Park while wearing your own inflatable costume. This unique Bronx event supports charity and takes place during a local ultramarathon for a high energy atmosphere.

A technical trail half and full marathon at University Settlement Camp in Beacon, NY on May 3, 2026, featuring steep, exposed climbs and substantial elevation gain with official aid stations and strict cut-off times.

A technical out and back 50K on New Haven blue trails with about 6,350 feet of climbing, strict time cutoffs, no crews or pacers, and multiple aid stations including water only stops.

A two-race trail event in Lyme CT on May 3 2026 with a 9.2 mile Moore Trail loop and a 3 mile Sprint, both chip timed. All proceeds support the Lyme Fire Department and the Lyme Ambulance Association.

A weekly cross country series offering thirteen 5K races on Tuesday nights from April to July. The event takes place at Central Park in Parsippany and is open to all ages and abilities. Participants can register for the full series or pay f..

A community trail run on May 9 at Clausland Mountain in Orangeburg, NY supporting mental health and sobriety, with three distance options, two aid stations, and optional shirts and medals.

A second annual 6k 3.8 mile cross country run at Bruynswick Winery in Gardiner, NY supporting the Ulster County SPCA. The day features music, a meet and greet with shelter animals, awards, and free children's dashes.

Spring Fling 600 in Southington, CT on May 9, 2026 features a 600 minute looped trail event and a 6 Mile race at YMCA Camp Sloper. Both events use chip timing and offer finisher medals and awards for top competitors.

The 20th annual Run for the Woods in Piscataway is a single-loop 5k through shaded trails at the Rutgers Ecological Preserve, with proceeds supporting forest restoration and student ecology groups; prizes include shoes and native plants.

A community event on May 9, 2026 featuring a Family Color Run and a 5K Trail Run at Hamden and New Haven YMCA locations. Registration runs from Feb 20 to May 8 with entry fees of $10 and $30; first 100 pre-registrants receive a Y giveaway.

A multi-day timed running festival at the Sussex County Fairgrounds featuring a certified 1.000 mile loop, multiple timed race durations, certified marathon and 50K options, on-course timing display, aid station kitchen, camping and RV faci..

Test your endurance on a 2.2 mile loop through the scenic Roosevelt Forest. This nine hour ultra event offers a supportive atmosphere for runners aiming to hit personal distance goals on classic New England trails.

A last person standing loop race on Ragged Mountain where runners repeat a roughly 3.11 mile loop and must finish each lap within one hour; entrants are eliminated if they fail to start or finish a lap, continuing until a single finisher re..

Trail races at Voorhees State Park on May 16, 2026 offering a 50k in five laps with UTMB index status and a 10k, both on marked trails with aid stations, on course amenities, and finisher medals.

Trail races in South Mountain Reservation on May 16, 2026 offering distances from a 1.15 mile kids race up to 50 miles and 50 kilometers. Forested east and west loops feature gravel roads, single track, aid stations and chip timing.

Experience a scenic trail run through the meadows and forests of Muscoot Farm. Choose from the 5 mile course or youth races and receive vouchers to spend at the local farmers market.