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.

Experience a technical 10 km trail race through the rugged terrain of Van Cortlandt Park in the Bronx. This annual event supports local trail maintenance and features unique local prizes for top finishers.

Run the perimeter of Heckscher State Park on smooth trails. Choose a 7-mile or 14-mile loop for a cupless, manually timed race. All finishers get a wooden medallion and a bucket hat.

Experience a scenic trail run through Bethpage State Park with the 4 Leaf Clover 5K. Enjoy a mostly flat course, post race refreshments, and a festive atmosphere supporting the Never Stop Running Foundation.

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..

Run or walk through scenic vineyards and orchards at this professionally timed 5k in the Finger Lakes. Enjoy cider and homemade donuts at the finish line of this annual community 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.

Experience a scenic 5K trail run through the vineyards of Spring Lake Winery in Lockport. Enjoy groomed trails and a post race celebration complete with a keepsake wine glass for all participants.

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 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.

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..