Trail Running calendar near Middletown Township 2026-2027

The 4th annual Chesterfield FALL Terrain 5K at Fenton Lane Park on October 18, 2026 features a 5K run/walk and a 1 mile Fun Dash, supports local charities, offers custom race shirts and age group awards.

Trail ultramarathon in Titusville, NJ with 50K and 25K courses that start and finish at Washington Crossing Park. The 50K features technical Rock Hopper trails and multiple aid stations.

A trail-based 5K and family 1 mile fun run in Poricy Park with a Halloween costume theme and prizes, raising funds for 180 Turning Lives Around. Options include a timed 5K, a fitness walk, and a family fun run.

A community 5K in Massapequa Park on October 24, 2026 featuring a scenic course through Massapequa Preserve, awards, post-race food and live results.

A trail event at Muscoot Farm on October 25, 2026: a five-mile race plus two kids races, kids medals, and Farm Bucks for finishers.

A fall running event in Garrison NY with a half marathon, a 5K and a 3/4 mile kids run on trails and roads through the Hudson Highlands.

The inaugural Barnyard Squatch 5K is a hilly trail race across The Barnyard Sanctuary's nearly 200-acre property in Blairstown, NJ, with over 500 feet of climbing and a route past rescued farm animals. All donations go to the sanctuary.

Obstacle course weekend at Sunflower Valley Farm near New Hampton NY with Sprint 5 km, Super 10 km, kids races, Hurricane Heat formats and spectator options.

A measured, professionally timed out-and-back race in Oaks PA on Nov 1, 2026 offering 10K, 5K and one mile options to support Tourette Syndrome awareness.

Experience a single loop marathon or half marathon on historic carriage roads in the Rockefeller State Preserve. Enjoy views of the Hudson River and stone bridges on a course with no pavement or cars.

Experience an off-road race weekend at Yeager’s Farm & Market featuring 4 and 10 mile trail runs. Enjoy a local atmosphere with post-race beer and bagels and earn a unique long sleeve tech shirt.

A trail 8K and 5K at Unionville Vineyards on November 8, 2026 with chip timing, live results, onsite music, post race wine, and awards. Walkers and children are welcome and the event includes water stations and post race amenities.

A timed trail event at Jacobsburg State Park on a roughly 5 mile loop of single track and gravel. The Fall Back edition runs the course in reverse and offers 5 mile, three-hour, and six-hour formats.

A trail and gravel running event in Wissahickon Valley Park offering 10 km, 10 mile and half marathon options with chip timing, aid stations, limited field size, and a post-race party with live music and warm food.

The Raven Rocks Run will take place in Cross River from Sunday 8 November 2026 to Monday 30 November 2026. You can run between 10 and 100 kilometers.

A community 5K and 1 mile walk on November 8, 2026 at Central Park of Morris County supporting Family Promise of Morris County, with in-person and virtual 5K options and age-group awards.

A charity trail event at Hillside Park on November 8, 2026, offering 10 km and 5 km races to benefit a free digital mammography program, with race timing, age-group medals and participant T-shirts.

A 6-mile trail race at Cheesequake State Park on November 8, 2026 with on-site registration, a post-race beer and pizza gathering, and proceeds benefiting local first aid and EMS organizations.

A community 5K run/walk at Belmont Lake State Park on November 8, 2026 with in-person and virtual options and proceeds supporting the Never Stop Running Foundation.

NYC Trail Mix is a trail running event in Staten Island on November 14, 2026, offering 50 mile, 50K and half marathon loop courses. The race benefits the Greenbelt Conservancy and uses three main aid stations with food and hydration options..