Trail Running calendar near East Islip 2026-2027

A 5K trail and obstacle run on the 400 acre campus of Gaylord Specialty Healthcare in Wallingford CT, featuring 24 obstacles and a festival area with vendors, live music, and food trucks, supporting the Gaylord Sports Association.

Experience a scenic evening run on a flat paved loop around Rockland Lake. This chip timed half marathon features sunset views, frequent aid stations, and custom finisher medals only 45 minutes north of NYC.

A six hour trail event at the Ansonia Nature Center with repeated counterclockwise 1.9 mile singletrack loops and about 170 feet of climb per loop. The 2026 edition was limited to 69 runners and was sold out.

A three zone athletic competition by Tone House on June 13, 2026 in New York. Individual, Doubles, and Team divisions combine timed runs, rowing, sleds, sandbag movements and a final Wild Card.

A community fundraising run at Van Cortlandt Park on June 13, 2026 featuring an in-person 5K, a virtual 5K option, and a free kids mile with proceeds benefiting local programs.

A community 5K and untimed 1-mile family walk at Camp Edey in Bayport supporting Girl Scouts of Suffolk County. The day includes family activities, finisher medals, event shirts, and awards while raising funds for scholarships and programs.

A community 5K trail run, walk, and hike at Eisenhower Park in Milford on June 14, 2026, on a high school cross country course. The event supports the Milford Rotary and Beth El Center and includes music, water, snacks, awards, and T shirts..

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..

Four Tuesday evenings of cross country racing at Grove 4 in Donaldson Park offering 5k, 2.5k and youth distances. Series and single race entries have tiered fees with member and youth discounts plus post race food and awards.

XTERRA TRANSCEND in Randolph NJ on June 20, 2026 features a half marathon, 10K and 5K on singletrack and lakeside trails. The half marathon is a 2027 XTERRA Trail Run World Championship qualifier and navigation via RideWithGPS is provided.

A morning trail run at Gay City State Park on June 20, 2026, offering 8 mile, 5 mile and 3 mile races. The 8 mile joins regional trail series and includes team competition with prize money.

The Jade's Belmont Plateau 5K will take place in New York on Saturday 20 June 2026. You can run 5 kilometers.

Three one mile races on track, grass and road at a single venue in Clark, New Jersey. Each mile is timed separately and cumulative times decide overall scoring, with two hours allotted to complete all three.

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..

Test your endurance at Roosevelt Forest on a 2.1 mile loop featuring classic New England terrain. Complete as many laps as you wish over 33 hours or aim for the 100 mile buckle in this intimate 50 runner event.

A 12 hour looped endurance event at Brooksvale Park in Hamden CT. Runners complete 3.1 mile loops with about 300 feet of gain and aid at each loop, with proceeds supporting local trail maintenance.

A 3.1 miles moonlight trail run at Lakeside Park in Pawling, NY with varied terrain, glow markers, required personal light, post run towel and a handmade finisher medal. Proceeds support the Pawling Recreation Department.

Experience a unique trail race through the Westmoreland Sanctuary where you choose your own path at the fork. Start and finish at Fox Lane High School for a memorable 5k adventure in Bedford.

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 trail event at Red Wing Recreation Area on July 5, 2026, offering 15K, 30K, and 60K options across a 15k loop with mixed terrain, on-course aid stations, post-race food, and awards for top finishers.