Trail Running Calendar New York 2026-2027

Mudders and Grunters is a trail race in Yorktown Heights on March 29, 2026, featuring an approximately 5 mile single loop through mud, water crossings and some hills. It is part of the 2026 Trail Mix Series.

A trail event in Van Cortlandt Park on March 29, 2026 featuring a hilly 10K and a 0.5 mile kids run. Partial proceeds support the Van Cortlandt Park Alliance and prizes include carrot cake and muffins.

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.

Experience a technical mountain trail race at Harriman State Park featuring steep climbs and rock scrambling. Choose between 10K and Half Marathon distances with stunning views of the Hudson Valley and NYC skyline.

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.

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 USATF certified point to point half marathon in Albany featuring a mostly downhill paved route along the Helderberg Hudson Rail Trail, six aid stations, live tracking every 5K, bus service to the start and a finisher medal.

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 spring trail race at Green Lakes State Park in Fayetteville NY with 50 km, 20 mile and 10 mile options on a 10.4 mile loop featuring varied terrain, two aid stations, and post race ramen with vegan options.

Shore2Shore is a point to point trail event on the Long Island Greenbelt Trail between Sunken Meadow and Heckscher State Park offering 50K and 25K distances with fully stocked aid stations and a required two hour trail work contribution.

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 20K trail run through Hi Tor Wildlife Management Area near Naples NY, the Muddy Sneaker features steep elevation changes and mixed trail hazards. Entry was capped at 200 runners and a tiered refund policy applied.

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..