Trail Running calendar near East Islip 2026-2027

A community 5K in Massapequa Park on October 24, 2026 featuring a scenic course through Massapequa Preserve, awards, post-race food and live results.

A trail event at Muscoot Farm on October 25, 2026: a five-mile race plus two kids races, kids medals, and Farm Bucks for finishers.

A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.

A fall running event in Garrison NY with a half marathon, a 5K and a 3/4 mile kids run on trails and roads through the Hudson Highlands.

Obstacle course weekend at Sunflower Valley Farm near New Hampton NY with Sprint 5 km, Super 10 km, kids races, Hurricane Heat formats and spectator options.

Looped trail races at Red Wing Recreation Area in Lagrangeville, NY offering 100k, 50k, and 10k courses with aid stations and finisher medals.

Timed trail event at Gurski Farm in Brookfield CT featuring an 8 hour race, a 4 hour option, and a 5K canicross on a 4 mile loop.

Experience a single loop marathon or half marathon on historic carriage roads in the Rockefeller State Preserve. Enjoy views of the Hudson River and stone bridges on a course with no pavement or cars.

A trail event at Ward Pound Ridge Reservation featuring a 10 km race, a November 100 km virtual challenge, rugged climbs, and fundraising for the Friends of Trailside Museum.

A 5k chip-timed run/walk at Stonington Vineyards on November 8, 2026 featuring a two-lap cross country route through the vines. Registration includes a shirt, collapsible wine glass, finisher medal and a pour of wine.

A community 5K and 1 mile walk on November 8, 2026 at Central Park of Morris County supporting Family Promise of Morris County, with in-person and virtual 5K options and age-group awards.

A 6-mile trail race at Cheesequake State Park on November 8, 2026 with on-site registration, a post-race beer and pizza gathering, and proceeds benefiting local first aid and EMS organizations.

A community 5K run/walk at Belmont Lake State Park on November 8, 2026 with in-person and virtual options and proceeds supporting the Never Stop Running Foundation.

Trail races on Staten Island with looped courses of 50 miles, 50K, and a half marathon that support the Greenbelt Conservancy.

Experience the diverse terrain of South Mountain Reservation with a looped trail race offering 5K, 10K, and half marathon distances. Enjoy a mix of single track and fire roads with support provided at regular aid stations.

A family-friendly 5K trail run and walk at Bethpage State Park on November 14, 2026 with in-person and virtual options and a free kiddie dash.

Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.

A scored 5K cross country race at Van Cortlandt Park on November 15, 2026, featuring youth programming, volunteer opportunities, live app tracking, and post-race awards.

A November cross country meet at Oak Ridge Park in Clark, NJ featuring 400m, 3K, 5K and 8K races, state championships for New Jersey, team titles for boys, girls and co-ed squads, and race amenities such as medals and free action photos.

Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.