Trail Running calendar near Brookfield 2025-2026

The Where the Pavement Ends Double Loop will take place in Ridgefield on Sunday 14 September 2025. You can run between 4 and 8 miles.

The Wild Goose Trail Festival takes place at Wawayanda State Park in Hewitt, New Jersey, offering a variety of trail running events over September 20-21, 2025. Distances range from a 1-mile kids run to a challenging 100-mile ultramarathon with a generous 36-hour cutoff, making it ideal for first-tim..

The Angevine Farm Trail Festival is a scenic trail running event held in Warren, Connecticut, in the picturesque Northwest corner of the state. The festival features multiple race options including an 8-hour endurance run, a half marathon, and 5K races with a Canicross option for runners with dogs...

The Gardiner Dump Run is a scenic trail running event held in Gardiner, New York, featuring a 5k race with an option to complete two laps for a 10k distance. The course winds through single-track trails along wooded hillsides near the Wallkill River and untamed fields at Gardiner’s Riverbend Trails,..

The Cockaponsett Trails to a Cure will take place in Chester on Sunday 21 September 2025. You can run between 4 and 9 miles.

The Cat's Tail Trail Marathon is a challenging 26-mile point-to-point trail race held in the Slide Mountain Wilderness Area of the Catskill Mountains, New York. Featuring nearly 7,000 feet of elevation gain, the course offers rugged terrain with rocky, technical climbs and descents, alongside stunni..

The Front Runners New York Cross Country 5K is an annual running event held at Van Cortlandt Park in the Bronx, New York. Celebrating its 22nd year in 2025, the race offers a scenic 5K cross-country course through the park's fall landscape. Participants meet at the iconic Tortoise & Hare Sculpture f..

The Caldwell Cougar Chase XC 5K & 8K is a cross-country running event held at Garret Mountain Reservation in Woodland Park, New Jersey. Scheduled for September 26, 2025, it features a women's 5K and a men's 8K race on a rolling course that includes trails, hills, gravel, dirt paths, grass sections,..

The Tunxis Trail Ultramarathon, held in Burlington, Connecticut, features challenging and technical trail races on the Tunxis Trail system, part of the Blue Blazed hiking trails. The event offers shorter distances this year, including an 8K (5 miles) and a 5K (3.1 miles), with staggered start times...

The Water Gap 50k and 25k is a scenic trail running event held in Milford, Pennsylvania, within the Delaware Water Gap National Recreation Area. The race courses follow the McDade Trail, a 32-mile route featuring a mix of rail-trail style cinder paths and singletrack terrain. Known for its rolling,..

The IronHike Endurance Series will take place in Cornwall from Thursday 2 October 2025 to Sunday 5 October 2025. You can run between 15 and 152 miles.

The NJ Trail Series One Day is a multi-day ultrarunning event held at the Sussex County Fairgrounds in Augusta, New Jersey. Scheduled from October 2 to 5, 2025, it features a variety of race options including 72, 48, 24, 12, and 6-hour timed races, as well as marathons and 50K distances. The course..

The CFA Trail 5K & Children's Fun Run for Mental Health is a timed trail running event held at Deans Mill Farm in Stonington, Connecticut. Participants can choose between a 5K trail run or a fun run for children aged six and under. The race takes place amid beautiful fall foliage, offering a scenic..

The Run the Vineyards - Pindar Fall 5K and 8K is a scenic autumn race held at Pindar Vineyards in Peconic, NY, featuring courses through 300 acres of vineyard property. Participants can choose between a 5K and an 8K race, both on mostly flat, hard-packed dirt trails and short-cut grass, making the e..

The Fat Sass Switchback Challenge is a trail running event held in Millburn, New Jersey, at the South Mountain Reservation's Locust Grove Picnic Area. Scheduled for October 5, 2025, it features a challenging 1-mile loop course with 300 feet of elevation gain, including steep climbs and technical, ro..

The KMT Fall Foliage Frenzy is a timed trail running event held in Montebello, NY, featuring 3-hour and 6-hour race options. Participants run on a challenging 2.33-mile loop course in Kakiat Park, adjacent to Harriman State Park, with approximately 660 feet of vertical gain per lap. The course offer..

The NipMuck Trail Marathon, held in Ashford, Connecticut, is a challenging 26.4-mile trail race along the scenic Nipmuck Trail. The course features diverse terrain including rocks, roots, mud, and wood bridges, offering a true test of trail running skills. Runners start at Perry Hill Road and naviga..

The Norfolk Land Trust Trail Race Series, including the Haystack Mountain Challenge, is held annually in Norfolk, Connecticut. The 12th edition features three trail race distances: a challenging 5K through Barbour Woods with scenic climbs and wetlands; a 10K that adds a tough loop summiting Haystack..

The Tesla Hertz Run is an ultramarathon event held in Rocky Point, New York, featuring multiple race distances including 150 miles, 100 miles, 100K, 50 miles, 50K, and 10 miles, with both daytime and nighttime options. The course is a scenic 10.48-mile loop through the pine barrens of Long Island, o..

The Forbidden Forest 30 Hour Ultra Run is an epic endurance event held in Stratford, Connecticut, offering runners up to 30 hours to complete distances ranging from a marathon (26.2 miles) to 100 miles or more. The course features a challenging 2.23-mile loop with roots, rocky terrain, and a notable..