Trail Running calendar near Upper Nyack 2026-2027

Multi distance trail event at Horseshoe Bend Park with a two mile loop, central Base Camp, night markings, and handcrafted wood awards.

A family friendly, obstacle filled beach 5k in Stratford that raises funds for Sterling Community Center while supporting individual and team fundraising.

Trail races of 70 mile, 30 mile and half marathon distances along the rugged, largely unsupported Shawangunk Ridge near Rosendale NY.

City Challenge Race returns to Jersey City on September 12, 2026 with a fast 3-mile urban obstacle course featuring 20+ city-style obstacles, new finisher medals, professional chip timing, awards and free race photos.

Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.

Trail race in Macedonia Brook State Park, Kent CT offering 12K, 25K and 50K loop courses with significant elevation, aid stations, and a cupless policy.

Timed 5k at Blue Ridge Estate Vineyard and Winery in Saylorsburg on Sept 13 2026, with event swag, an on course wine pour, age group awards, and virtual options.

The Corporate Fun Run Pier 84 Manhattan will take place in New York on Monday 14 September 2026. You can run 5 kilometers.

Timed trail races in Pawling NY offering 24, 12, 6 and 3 hour options on an approximately 1.68 mile loop with on course aid and athlete camping.

A multi-day trail running festival in Ringwood State Park offering events from a 1 mile kids race to a 100 mile ultramarathon and community support programs.

A USATF-sanctioned trail event in Upper Nyack with a 50 mile option featuring four 11.5 mile loops, about 9,700 feet gain, and three aid stations.

Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.

A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.

Point to point 26 miler in the Slide Mountain Wilderness with nearly 7,000 feet of vertical gain and multiple aid stations; proceeds support land conservation.

A 50K and 25K trail event on the McDade Trail in Milford PA, out and back along the Delaware River with three aid stations and a cupless course.

A 5th annual 3.1-mile run and 1.1-mile walk at The Church of St. Andrew in Staten Island, and the first leg of the Staten Island FALL TRIFECTA.

Technical trail races in Burlington CT on the Tunxis Trail offering 8K and 5K courses that pass the CT State Trout Hatchery and Nassahegan State Forest.

A trail running event in Gardiner, NY offering a 5 km run, an optional 10 km two-lap route and a 200 yard kids run, with pre registration T shirt incentives and a sneaker recycling program.

A six-hour run and relay at Belmont Lake State Park honoring Fred von der Heydt with individual and team competition on a 1.50 mile loop and commemorative apparel.