Trail Running calendar near Fairfield 2025-2026

The Wahaneeta Trail Run is a 5K trail race taking place in Westerly, Rhode Island, as part of the WTAC Fall Race Series. This event emphasizes a "no frills" approach, foregoing modern amenities like t-shirts and extensive awards to keep costs low and logistics simple. Participants can enjoy a classi..

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 Charlie Stavros Memorial Beach Run is a free, end-of-summer 3-mile running event held at Westerly Town Beach, Rhode Island. Organized by the Westerly Track Club and the Stavros family, the race features a scenic route that includes a 1.5-mile out-and-back course along the beach at low tide. This..

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 Angevine Farm Trail Festival, located in Warren, Connecticut, offers an exciting day of trail running amidst the scenic beauty of the Northwest corner of the state. Participants can choose from various race options, including a 5K, a 5K Canicross (running with dogs), a Half Marathon, and a new 8..

The IronHike Endurance Series, taking place at Mohawk Mountain in Cornwall, CT, is a unique multi-day event designed for both individual participants and teams. Scheduled for October 2-5, 2025, it features various challenges, including the Kuwohi, Double K, Denali, Everest, and Olympus Mons Ultra, e..

The Run for the Pumpkins Trail Run, organized by the Westerly Track & Athletic Club, is part of the WTAC Fall Race Series and will take place at Bradford Preserve in Westerly, Rhode Island. This event features a 10K, a 5K, and a children's 1K run for participants aged 10 and under. The courses showc..

The Nipmuck Trail Marathon, taking place in Ashford, CT, is a challenging 26.4-mile race that showcases the rugged beauty of the Nipmuck Trail. Participants can choose between the full marathon or a relay option, where two runners split the course. The race features a mix of terrain, including rocks..

The Run the Vineyards - Pindar Fall 8K is a scenic running event set in the picturesque Pindar Vineyards in Peconic, NY. Participants can choose between an 8K and a 5K race, both featuring flat courses primarily on hard-packed dirt trails and grass, making them walker-friendly. The event includes ch..

The Tesla Hertz Run is an exciting running event taking place in Rocky Point, NY, featuring various race distances including a 150 Miler, 100 Miler, 100K, 50 Miler, 50K, and 10 Miler. Set in a picturesque area of Long Island, the course offers a scenic 10.48-mile loop with minimal outside interactio..

The Forbidden Forest 30 Hour Ultra Run is an exciting endurance event set in Stratford, CT, where participants can run, power-hike, or walk for up to 30 hours. This ultra run offers various distance options, including 26.2 miles, 50K, 50 miles, 100K, and 100 miles, allowing athletes to challenge the..

The Mohawk Mountain Race, organized by Steep Endurance in collaboration with Mohawk Mountain Ski Area, offers a thrilling trail running experience set against the backdrop of stunning fall foliage. Participants can choose from various distances, including 5K, 10K, Half Marathon, and Marathon, with p..

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 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 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 Grills Trail Run, organized by the Westerly Track & Athletic Club, is part of the Fall Race Series and features both 10-mile and 10K races. Set in the scenic Grills Preserve in Westerly, Rhode Island, the event showcases beautiful trails, bridges, and riverfront areas, with a course comprising a..

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 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 ..