Trail Running Calendar New York 2026-2027

Experience a community trail event in Cross River featuring a competitive 5k race, a scenic 4k walk, and a 200m kids dash. Explore the wooded hills of the John Jay Community Trail ending at the campus contest field.

A six hour run or walk on the Amherst Bike Path where participants cover as many laps as they choose. USATF certified half and full marathon options run concurrently and all finishers receive a medal.

Experience a beautiful trail run through the Irvington Woods with 5K and 1K distances. This rain or shine community event features finishers medals for all participants and supports the Irvington Bulldog Booster Club.

A mid-April trail race at Green Lakes State Park with 10.4-mile loops, roughly 1,300 ft gain, three distances, on-course aid stations, and post-race ramen with vegan options.

Complete as many one mile loops as you choose during this 24 hour endurance challenge in Fairport. Enjoy a fully stocked aid station and a supportive community environment at Fellows Road Park.

A point-to-point trail race on the Long Island Greenbelt Trail with 50K and 25K options, fully stocked aid stations, parking at Heckscher Park, and a two-hour trail-volunteer requirement for entrants.

The final Conquer the Trail Race is a 7.5 km run on the flat Croton Aqueduct Trail. This special edition supports Mercy University's Mav Market and celebrates the school's 75th anniversary. The event offers awards, raffles, and free parking..

A rugged 20K (twelve-plus mile) trail run at Hi Tor Wildlife Management Area near Naples, NY, noted for steep elevation changes and technical terrain. The field is limited to 200 runners and a defined refund schedule applies.

Run or walk through the scenic orchards of New Paltz at this chip timed 5k event featuring homemade donuts and fresh cider for all finishers.

The Brookhaven Trail 15K and 4 Mile runs explore the varied paths of Brookhaven State Park. This cupless event is capped at 250 runners and includes awards, refreshments, and supports veterans and local food banks.

A five-week open-course trail running series in Poughkeepsie, NY, presented by Fleet Feet Poughkeepsie and powered by HOKA. Limited to 65 participants; registration runs March 18 to April 20, 2026 with a $60 fee.

Event Overview The Squatchywaska Mountainfest is a trail running event with two distances: a 25K (noted as closer to 17 miles) and a 10-mile race. Both courses follow a lollipop format through Minnewaska State Preserve on the Shawangunk Rid..

A spring trail race at Grafton Lakes State Park covering about 9.3 miles with roughly 900 feet of elevation gain. Trails are technical yet runnable and the course can be muddy in spring.

Celebrate spring in the Adirondacks with a scenic half marathon or a family friendly 5k trail race. Support local healthcare while following a historic route from Keene Valley to Elizabethtown.

A 5K road and trail run at SUNY Morrisville on April 25, 2026 supporting student development in conservation and environmental science. The event features a tree planting, trail sections that may be muddy, awards by age group, and shirts.

A spring trail race in Cross River, NY on April 26, 2026 offering a 10K course with entry by lottery. The $56 registration fee includes park entry and the race is USATF sanctioned; dogs are not allowed to run in the event.

A community 5K on April 26, 2026 in Croghan NY offering walk, bike, and run options, with a pancake breakfast included and no official timing.

Try the Trail is a youth trail run for ages 4 to 16 at Katonah Memorial Park. Kids can choose between a half-mile or one-mile course on scenic, easy-to-follow trails. It's a family-friendly event focused on outdoor activity.

Experience a monthly trail running series through the scenic landscapes of Mendon Ponds Park. Each event features timed races of varying distances followed by a social gathering with pizza and drinks.

An ultramarathon in Van Cortlandt Park featuring an initial flat lap plus ten cross country loops, stocked aid stations, drop bag access, and finisher awards including a medal, singlet, meal and post race beer.