Trail Running calendar near Hauppauge 2026-2027

ENDURE Last Man Standing in Bethpage State Park asks runners to repeat a fixed 4.2 mile loop each hour; finish within the hour to continue. Laps continue with progressively shorter cutoffs until one runner remains or the event window ends.

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

A timed 5K trail race at Coogan Farm in Mystic, running through meadows, woods, and fields, with limited entry, tiered fees, an awards ceremony, and opportunities to meet Nature Center animal ambassadors.

A two day family obstacle event at Obstacle Wonderland in Wallkill featuring adult sprint and multi lap endurance formats, plus kids 50 m and 1 km courses, finisher medals, podium awards, and a charity presence.

A repeat-loop trail race at Tatum Park in Middletown, NJ offering 1-lap, 30 km, and 50 km options with one main aid station and RFID lap timing. Proceeds support MissionCleanWater's clean water programs.

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 weekly Tuesday evening cross country series at Waveny Park with varied distances and formats, including predicted time races, relays, handicaps, a luminaria finish, and age-graded awards.

A multi-day elevation endurance series at Mohawk Mountain in Cornwall Connecticut from June 4 to 7 2026. Events range from a 12 hour 15 mile challenge to 84 hour ultras with solo and team FlexRelay formats.

Experience a timed 5K trail run or walk through the scenic woods and fields of the Van Vleck Farm and Nature Sanctuary. Enjoy live music and food trucks at this annual community event in Woodbury.

A non competitive group run along the D&R Canal Towpath with paced "trains" and multiple distances. The event benefits the Rutgers Cancer Institute with a $0.50 donation per mile and offers bus starts and a picnic option.

A road and trail event at Rockwood Hall in Rockefeller State Park Preserve featuring a 10K and a 1K kids race. The course follows wide carriage roads with Hudson River views and wooded sections, and proceeds support carriage road maintenanc..

On June 6, 2026 at Rockland Lake State Park, the event offers a scenic 5K paved loop with a wheelchair division and a rugged 10K mountain run climbing 1,300 ft on technical trails.

A women only 5K obstacle mud run in Long Island on June 7, 2026, held at Dorothy P. Flint 4-H Camp. The course features more than 18 obstacles and welcomes participants aged seven and older in a non competitive, team focused setting.

A free trail 5K in Shirley Chisholm State Park in Brooklyn on June 7, 2026, organized by Black Men Run NYC. Registration is free with an optional $25 singlet fee and runs March 31 to June 4, 2026.

Trail races at Ward Pound Ridge Reservation on June 7, 2026 include a 13.1 mile half marathon and a 10K, both passing the summit where the historic fire tower is being reconstructed. The event also raises funds for the Friends of the Fire T..

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 free community trail event in Farmington offering shoe demos and short runs on local trails. Options include about 5 km, 1.7 mile, and 1 mile routes, with snacks and drinks afterwards.

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 looped trail run at Ansonia Nature Center on roughly 1.9 mile counterclockwise singletrack loops with about 170 feet of gain per loop. Field capped at 69 runners; no crews or pacers; early signup includes a shirt and swag.