Trail Running calendar near Hauppauge 2026-2027

Experience the eighth annual Spring Fling 600 trail races at YMCA Camp Sloper. Choose between a 6 mile race or a 10 hour challenge to complete as many loops as possible on a scenic three mile course.

A loop-based last person standing trail event on Ragged Mountain in Berlin CT with roughly 3.11 mile laps to be completed within an hour; field limited to 55 and proceeds benefit local trail groups and a youth shoe scholarship program.

Trail races in South Mountain Reservation on May 16, 2026, from 5 miles to 50 miles plus a Kids 1 Mile; looped courses, aid stations about every five miles, and volunteer-run proceeds support the Conservancy.

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.

A technical trail race in Norvin Green State Park offering 50K, 10 Miler and 5 Miler courses over steep terrain, boulder fields and river crossings. The event is cupless, has aid stations and specific mandatory gear for the 50K.

Run a 3.5-mile trail race in Wolcott, CT. The event supports the local cross country teams. Your entry includes access to the CT Food Truck Battles Festival afterward.

Experience Long Island trail running with a full marathon or 15 mile race at Bethpage State Park. Support the local Greenbelt Trail Conference while exploring the natural paths of Farmingdale.

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..

Experience a refreshing spring trail run or walk through the scenic paths of Blydenburgh County Park. Enjoy a 5K course featuring dirt roads and wooded trails followed by delicious refreshments and professional finish line photos.

Mine Hill Half Marathon is a 13.1 mile road race in Roxbury, Connecticut, with start and finish at Mine Hill Distillery. The course passes farms, fields and scenic vistas and includes a post-race gathering at the distillery.

A 4 mile out-and-back road and trail race in Forest Park, Queens on May 24, 2026, starting and finishing at Victory Field Track; entries capped at 500, guaranteed technical shirts for pre-registrants, custom medals for finishers and cash aw..

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..

ENDURE is a Last Man Standing running event where participants complete a fixed loop every hour. The last runner standing wins, with a central hub for recovery and community. It's designed for all levels, from seasoned endurance athletes to..

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.

Experience a timed 5K trail race through the scenic meadows and woods of Coogan Farm in Mystic. Enjoy post race festivities with animal ambassadors and support local environmental conservation at this inaugural event.

Test your skill and grit at a permanent outdoor obstacle facility in Wallkill. Explore a variety of competitive sprints and non-competitive endurance courses for both adults and children over a two-day weekend.

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 limits at this multi day vertical endurance series at Mohawk Mountain. Choose from seven elevation based challenges ranging from 12 to 84 hours as an individual or part of a flexible relay team.

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.

Join a unique non competitive group run along the D&R Canal Towpath with various distances and pace groups. Support the Rutgers Cancer Institute while running in a guided train formation to a celebratory picnic.