Trail Running calendar near Milford 2025-2026

The Horseshoe Bend Boogie will take place in Frenchtown on Saturday 16 August 2025.

The Barn-B-Q Trail Festival is a unique outdoor celebration held at the restored Masker's Barn in Berkeley Heights, NJ. This event combines trail running and hiking with a lively barn party featuring BBQ, beer, wine, and various activities. Participants can enjoy self-guided trail tours, lawn games,..

The Macedonia Trail Race, held annually in Macedonia Brook State Park, Kent, CT, offers a unique trail running experience with stunning single-track paths, challenging climbs, and breathtaking viewpoints. Celebrating its 7th year, the event features three race distances: 50K, 25K, and 12K, catering ..

The Boulder Field 100 is a challenging running event taking place in Hickory Run State Park, Jim Thorpe, PA. Participants can choose from three distances: a 100K ultra run, a 50K ultra run, and an 18-mile run/hike. The course features a rugged terrain with an estimated elevation gain of 4000 feet pe..

The Pawling 24 Hour Trail Running Festival is an exciting endurance event taking place in Pawling, NY, featuring a variety of race options including 24-hour, 12-hour, 6-hour, and 3-hour challenges. Participants will run on a scenic loop course that combines pavement, grass, and single track trails, ..

The Shawangunk Ridge Trail Run (SRT) is a scenic running event that takes place along the 70-mile Shawangunk Ridge Trail, which spans from High Point State Park in New Jersey to Rosendale, New York. The event features three divisions: a 70-mile ultra, a 30-mile run, and a half marathon, catering to ..

The Wild Goose Trail Festival, taking place from September 20-21, 2025, at Wawayanda State Park in Hewitt, NJ, offers a variety of trail running events, including distances from 1 mile to 100 miles. This festival features a supportive atmosphere with generous cut-off times, making it ideal for both ..

The Gardiner Dump Run is an exciting running event scheduled for September 21, 2025, in Gardiner, NY. Participants can choose between a 5k trail run or a 10k option, which consists of two laps of the 5k course. The race takes place on scenic single-track trails through wooded hillsides near the Wall..

The Water Gap 50k and Half is a scenic trail running event set in the picturesque Delaware Water Gap, Pennsylvania. Participants can choose between a 50K or 25K distance, both of which traverse the beautiful McDade Trail, known for its mix of cinder paths and singletrack terrain. The event celebrate..

The Cat's Tail Trail Marathon is an exciting point-to-point trail marathon set in the stunning Slide Mountain Wilderness Area of the Catskill Mountains, New York. Scheduled for September 27, 2025, this challenging race features nearly 7000 feet of elevation gain, offering participants breathtaking v..

Blackout is an exciting nighttime running event taking place in Emmaus, PA, featuring a challenging 10K course that navigates the rugged, mountainous terrain of South Mountain. Participants can choose to start the race at dusk or take on the full experience under the stars. The event emphasizes sust..

The Lehigh Gap Nature Center 10K is an exciting trail running event taking place in Slatington, Pennsylvania. Celebrating its 14th year, this year's race features a brand new loop course that showcases the stunning natural beauty of the Nature Center. Runners will experience a mix of flat and steep ..

The Paine to Pain Trail Half Marathon is a unique running event set in the scenic woods and trails of five parks in Westchester County, New York. This race features a single-loop course that allows participants to experience diverse terrain, primarily consisting of dirt paths, while enjoying the nat..

Big Bear Squatchtoberfest is a trail running event hosted by Sassquad Trail Running in collaboration with the New York-New Jersey Trail Conference. Set in Harriman State Park, Tuxedo, New York, this event features a challenging half marathon and a 10K race, showcasing the park's rugged terrain and s..

Run The Farm is a running event taking place at Muscoot Farm in Katonah, NY, featuring a 5-mile trail race and two kids' races. Scheduled for October 19, 2025, the event includes a 5-mile race for participants aged 6 and up, along with two kids' races: one for ages 7-12 and another for children aged..

The "8 Hours at the Farm" is a trail running event organized by Steep Endurance, taking place at Gurski Farm/Williams Park in Brookfield, CT. This race features a scenic, approximately 4-mile loop that includes single track and rolling farm trails, fostering a vibrant community atmosphere among part..

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. Participants will enjoy scenic, rolling courses with views of the Hudson River, featuring fields, stone walls, lakes, and forests. This event supports local organizations, including the ..

The Tarrywile Half Marathon is recognized as one of the most challenging trail half marathons, featuring nearly 3,000 feet of elevation gain and technical Northeast single track terrain. The course offers stunning views of Danbury and serene lakes within Tarrywile Park. Participants can choose from ..

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 aims to ..