Trail Running calendar near Sleepy Hollow 2026-2027

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.

Experience a clockwise loop race at South Mountain Reservation featuring timed options from one to six hours. This event offers a 1.88 mile course consisting of single track paths and fire roads for all distance preferences.

Experience the single track and gravel trails of Jacobsburg State Park in this zero carbon event. Choose between a fixed five mile loop or timed sessions of three and six hours.

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 an authentic off road adventure in Guilford with a 10k trail loop featuring technical single track paths and rock scrambles through Westwoods to support local land conservation.

Run a unique quarter marathon distance on the paved trails of West Hartford Reservoir. This chip timed 6.55 mile race features a two loop course with post race treats and age group awards.

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.

Run or walk the scenic trails at Institute Woods. This 6K event offers a shorter 3K option for walkers and is limited to 200 participants. Post run refreshments await all finishers.

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 unique all terrain run through Heckscher Farm and wooded trails in Stamford. Runners pass farm animals and historic landmarks on a scenic course while children enjoy a dedicated fun run and educational activities.

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.

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.

Trail loops at Penwood State Park near Bloomfield CT, with a **50K** (three loops) and a **17K** (one loop) on mixed technical single track and double-track terrain; the 50K has a nine hour cutoff.

A 5K cross-country run at New Jersey's first farm brewery. The course winds through the scenic grounds of Screamin' Hill Brewery. All finishers get a coaster medal, and the after-party includes live music and a food truck.

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..

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.

Experience a complete Trifecta weekend at Vernon Peak with obstacle courses ranging from 5K to 50K. Test your grit on northern New Jersey mountain terrain featuring vertical climbs and over 60 obstacles for the elite Ultra distance.

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..

Trail running in Wawayanda State Park on April 25, 2026, with multiple distances and a 26+ mile loop through rhododendron tunnels and marsh bridges. Aid stations, onsite camping and a central BaseCamp provide support for crews and pacers.