Trail Running calendar near Milford 2025-2026

Big Bear Squatchtoberfest is a trail running event hosted by Sassquad Trail Running and the New York-New Jersey Trail Conference, taking place at Harriman State Park in Tuxedo, New York. Participants can choose between a challenging half marathon and a 10K, both featuring rugged terrain, steep climb..

Run The Farm is a trail running event scheduled for October 19, 2025, at Muscoot Farm in Katonah, NY. The event features a 5-mile race for adults and two kids' races: one for ages 7-12 and another for children aged 6 and under. Participants can enjoy the scenic beauty of the farm while promoting awa..

WXT Ultra is an exciting running event taking place in Washington Crossing Park, NJ, featuring two challenging distances: a 50K and a 25K+. The course includes scenic single-track trails, road sections, and a historic finish on the Continental Trail. Participants will navigate through beautiful land..

The Fall Back Into The Trails Series is an annual running event hosted by C.T.W Endurance at the Red Wing Recreation Area in Lagrangeville, NY. Scheduled for November 1-2, 2025, this event features three race options: a challenging 100k, a 50k, and a 10k, with varying elevation gains. The series is..

8 Hours at the Farm is a trail running event organized by Steep Endurance, taking place at Gurski Farm/Williams Park in Brookfield, CT. Participants can choose from three race options: an 8-hour endurance challenge, a 4-hour option, or a shorter 4-mile race. The course features a scenic 4-mile loop..

The Long Run - Fall Back is a unique running event taking place at Jacobsburg State Park, featuring a 5-mile loop on a mix of single track and gravel trails. Participants can choose to compete in a 5-mile race, a 3-hour, or a 6-hour event, with the course run in reverse for this rendition. The event..

The Pocantico Hills Marathon, taking place in Rockefeller State Park, offers both a marathon and a half marathon on scenic, rolling courses with stunning views of the Hudson River and Palisades. Participants will enjoy a picturesque route featuring fields, stone walls, lakes, and forests. This event..

The Raven Rocks 10k is an annual trail race held at the Ward Pound Ridge Reservation in Cross River, NY. Scheduled for November 9, 2025, this challenging course features rocky climbs, ridgeline trails, and scenic views, making it a favorite among trail running enthusiasts. Participants can also join..

The Tarrywile Half Marathon is a challenging trail race set in Tarrywile Park, Danbury, Connecticut. Known for its tough terrain, the course features close to 3,000 feet of elevation gain and technical Northeast single track paths, offering stunning views of the surrounding area. Participants can ch..

The Squatchy Leftovers Trail Race, taking place on November 29, 2025, at South Mountain Reservation in West Orange, NJ, offers a variety of distances including 5K, 10K, 25K, and 50K. This family-friendly event supports the non-profit organization Bigger Than The Trail, which provides cost-free thera..

Rob's Trail Run Edition is a running event taking place at Stillwell Woods Preserve in Woodbury, NY. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run and a 5K High School or Youth Trail Run, catering to participants of different age groups. This event not only..

The Holmdel Classic is an end-of-year 50K trail race held in Holmdel Park, New Jersey, designed to challenge participants' mental and physical endurance. The course features seven loops totaling approximately 32.55 miles, with a mix of terrain and significant elevation gain. This event not only test..