Trail Running calendar near Massapequa 2026-2027

A novelty one mile event on December 6, 2026 in West Orange, NJ combining four cycles of drinking eight ounces of egg nog while stationary then completing a quarter mile loop. Dairy and Non-Dairy divisions are offered.

A December trail ultra in Holmdel Park, New Jersey using a just over 4.5 mile loop repeated for Halfish and 50 kmish distances. The event supports MissionCleanWater and uses RFID lap timing with an aid station at the start and finish.

A weekend trail event in Blydenburgh County Park featuring a Backyard Ultra with 4.167 mile hourly loops and a separate 4.16 mile lapping race. A portion of proceeds supports the Long Island Greenbelt Trail Conference.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

Trail races at South Mountain Reservation include 5K, 10K and 13.1 mile looped courses with aid stations every 3 miles. Courses use fire roads, single track, hills and some pavement and offer advance and day-of registration.

A January trail party in West Orange with a 5K loop plus timed 3 and 6 hour options, rucking divisions, and fundraising for the South Mountain Conservancy.

A onesie-themed trail 5K at Ramapo Valley County Reservation featuring a flat, scenic loop around Scarlet Oak Pond and accessible course options.

Trail races on a 10 mile loop at South Mountain Reservation offering 50M, 50K, 20M and 10M with marked trails, three aid stations per loop, timing, SWAG, and awards for top three male and female finishers.

Timed loop races at the Livingston Oval offer 1, 3, 6 and 12 hour options on a USATF certified flat course, with aid station support, awards for top finishers, and participant cap or hat with a no-swag discount available.

Looped trail race in South Mountain Reservation offering 11M, 20M, 50K and 50M over three marked loops with varied terrain and on-site aid.

Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and f..

A six-hour trail ultra at Roosevelt Forest featuring a 2.3-mile loop with 191 feet of climb per lap, chip-timed laps, on-course aid and food, podium awards, medallions for over four hours, and a limited field supporting local charities.

The Rat Race 50k is a 100% off-road ultramarathon at Wells Mills Park with an 8-mile loop plus three 10k loops, chip timing, finisher medals and age-group awards; the series also includes shorter trail races and themed events.

A late-March trail event at Bethpage State Park offering a 5K trail run, a free kiddie fun run, race shirt, on-site refreshments and a virtual participation option.

A community 5K run and free kiddie run at Bethpage State Park with trail terrain, a virtual option, and donations benefiting the Never Stop Running Foundation.

A mountain trail event at Harriman State Park near Bear Mountain on April 3, 2027 offering 10K, 10K ruck and 13.1M courses on rugged, technical singletrack with marked routes, aid stations, rucking divisions, and adaptive support.

Trail races on a 25K loop at Sleeping Giant State Park featuring technical singletrack, steep rock scrambles, and an optional second loop for the 50K.

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY on mixed surfaces through park trails. The event supports Last Chance Animal Rescue and includes onsite hydration, restrooms, same day results and photos.

Shore2Shore in East Islip, NY on April 17, 2027 follows the Greenbelt from north shore to south shore and offers 50K and 25K distances.