Trail Running calendar near Wallkill 2026-2027

A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.

Inwood Hill Turkey Trot is a community 5K run/walk through Inwood Hill Park in New York City, offering live result updates, free finish line photos, awards for the top two men and women, and proceeds that support the Inwood Food Pantry.

A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.

A November trail party at South Mountain Reservation offering looped distances from a Kids 1M to a 50K, varied carriage roads and singletrack, on-course aid at the start/finish, adaptive support, and a charity partnership with Bigger Than T..

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

A repeated 3.3 mile out and back on the Tower Trail at Sleeping Giant State Park, with four hour and eight hour options and a cupless aid station at start and finish.

Trail races at South Mountain Reservation feature 5K, 10K and 13.1 miles on looped courses over fire roads, single track, hills and pavement, with aid about every three miles and race day registration available.

An ultramarathon in Prospect Park, Brooklyn on December 6, 2026 offering 50K and 50 mile looped courses with potluck-style aid, Skratch Labs hydration, chip timing, and finisher belt buckles.

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.

Celebrate the holidays with a scenic run through the historic Shawnee Inn golf course and wooded trails. Enjoy live music and a complimentary craft beer at the ShawneeCraft Brewery finish line.

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.

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.

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.