Trail Running calendar near Chester 2025-2026

The Anchor Down Ultra is a prestigious ultra-marathon event held at Colt State Park in Bristol, Rhode Island. It features three race durations: 6-hour, 12-hour, and 24-hour, catering to various levels of endurance runners. Recognized as one of the "Best Races in America" by Men's Health Magazine, th..

The Stonington Cross Country 5K is a running event scheduled for August 13, 2025, in Pawcatuck, Connecticut. This race features a 5K course and a Children's 1/2 Mile, catering to participants of all ages. The race begins on the track at Stonington High School, followed by a scenic route that include..

The Jug End Loop Ultra is an exciting running event scheduled for August 23, 2025, at Jug End State Reservation in Egremont, MA. Participants can engage in a 6-hour ultra event, completing as many laps as possible on a scenic 4.2-mile course that features a mix of uphill and downhill terrain. The ev..

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

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 Wine Run at Westport Rivers Vineyard & Winery is a unique running event scheduled for September 14, 2025, in Westport, MA. Participants can enjoy a scenic 3-mile trail run through the vineyard, followed by an evening of dinner, wine, and live music. The event is designed for individuals aged 21 ..

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 Cockaponsett Trails to a Cure is a trail running event taking place in Chester, Connecticut, featuring two race options: a 4-mile and a 9-mile course through the scenic Cockaponsett State Forest. The challenging terrain includes roots, rocks, and hills, with water stations provided along the rou..

The Angevine Farm Trail Festival, hosted by Steep Endurance, takes place in Warren, Connecticut, showcasing the region's scenic trails and beautiful fall foliage. This annual event features a variety of races, including a Half Marathon, 5K, and a unique 8-hour challenge, all set against a backdrop o..

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, 5K, and a children's 1K run for participants aged 10 and under. The courses showcas..

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 variety of terrains, including ..

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 primarily through pine barrens,..

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 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..

The Mohawk Mountain Race, organized by Steep Endurance, takes place at the Mohawk Mountain Ski Area in Cornwall, CT. This unique event transforms the ski mountain into a challenging running course featuring 5K, 10K, Half Marathon, and Marathon options. Participants will navigate steep ascents and de..

The Mt. Tom Trail Race, organized by Beast Coast Trail Running, offers participants a chance to explore the scenic beauty of Mt. Tom during peak foliage.The event features challenging courses, including a solo 25k, a 2-person relay, and a solo 10k, all set within the rugged terrain of Mt. Tom State ..

The Suffolk County Marathon is an annual running event held in Bay Shore, New York, featuring a variety of races including a full marathon, half marathon, 10K, and 5K. Scheduled for October 18-19, 2025, the marathon and half marathon take place on Sunday, while the 5K is held on Saturday. The races ..