Trail Running Calendar New York 2026-2027

Run or walk through 50 acres of beautiful vineyards in Peconic for a chip timed 5K event. Participants receive a finisher medal that doubles as a wine stopper and a celebratory pour of wine at the finish line.

This trail race offers a rugged 10k course through historic Van Cortlandt Park in the Bronx. A free Kids Fun Run is also part of the event. Part of the registration fee supports local trail maintenance and youth programs.

Experience the scenic trails of Heckscher State Park in this perimeter loop race offering 7 and 14 mile distances. Enjoy a cupless event with wooden medals and unique bucket hats for all finishers.

Tackle the rugged trails of Harriman State Park in this mountain trail run. Choose between a challenging 10K with 1,400 feet of climb or a half marathon with over 2,600 feet. The event supports local trail maintenance and includes a rucking..

Experience a scenic two lap cross country 5K through the vineyards and orchards of the Finger Lakes. Enjoy cider donuts and hard cider at the finish line of this professionally timed annual event.

Experience the 7th Annual Bunny Trail 5K at Bethpage State Park. Run or walk through scenic soft trails and grassy polo fields with options for an in person race, a virtual challenge, and a free kids run.

This scenic 5K trail run takes place through the vineyards and groomed trails of Spring Lake Winery in Lockport. All finishers receive a keepsake wine glass, with awards for top runners. An optional adult Easter egg hunt adds to the post-ra..

Test your endurance at Durand Eastman Park during this six hour event. Run a one mile loop that switches direction halfway through to see how much distance you can cover.

Join this dog friendly 5K trail run at Blydenburgh County Park to support animal rescue. Enjoy a scenic multi surface course with refreshments and professional timing included for all participants.

A fast, point-to-point half marathon descending from Slingerlands to the Hudson River in Albany. The course features paved rail trails and offers amenities like live tracking, gear check, and a post-race celebration. A free shuttle bus mana..

Experience the John Jay Community Trail Race in Cross River featuring a hilly 5k trail run a 4k walk and a kids dash. Support a local community trail built by volunteers while enjoying a course through woods and campus fields.

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.

The English's Ridge Rumble is a spring trail race in scenic Green Lakes State Park. Runners can choose from 10-mile, 20-mile, or 50km distances on a loop course with varied terrain. This USATF-sanctioned event is known for its views of the..

The Shore2Shore is a scenic point-to-point trail run on Long Island's Greenbelt Trail, from the north to south shore. Choose between the 50K or 25K distance on this well-marked course. Registration includes a trail work volunteer requiremen..

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..

The Muddy Sneaker is a 20K trail run in New York's Hi Tor Wildlife Management Area. Known for its rapid elevation changes, runners face a course with natural obstacles. Registration is capped at 200 with no waitlist.

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.

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..

The Grafton 15K is a spring trail race through the technical and muddy terrain of Grafton Lakes State Park. The 9.3-mile course features 900 feet of elevation gain, starting and finishing at the park's beach.