Trail Running calendar near Randolph 2025-2026

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 Frosty Forest 5K is an exciting trail running event taking place in Roosevelt Forest, Stratford, CT. Participants can run, jog, hike, or walk the 5K course while enjoying the beauty of nature and the festive holiday spirit. Costumes are encouraged, adding to the fun atmosphere.Awards will be giv..

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..

Naked Nick is a trail running event taking place in Leesport, PA, featuring two distances: a 25K and a 50K. The race course winds through the scenic trails of Blue Marsh Lake, offering a mix of single track and gravel roads. Participants can expect a friendly atmosphere with awards for the top finis..

The Frosty Looper 8-Hour is an exciting running event taking place at Cooper River Park, featuring a fast and flat 3.75-mile loop with scenic views of the Philadelphia skyline. This race is ideal for both seasoned ultra runners and those aiming to set personal records. Participants have eight hours..