Trail Running Calendar Connecticut 2025-2026

The Soapstone Assault is a challenging trail running event that takes place around Soapstone Mountain, covering approximately 5 miles. Participants will tackle a rigorous course that requires them to ascend the mountain six times, making it a demanding hill workout. The race features steep, rocky, a..

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

The Tarrywile Half Marathon is renowned as one of the toughest trail half marathons, featuring nearly 3,000 feet of elevation gain and technical Northeast single track terrain. Set in Tarrywile Park, the course offers stunning views of Danbury and its serene lakes. Participants can choose from three..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Connecticut, featuring a scenic course that ascends over 600 feet to the Observation Tower. Participants can choose between 4-hour and 8-hour options, completing loops on the Tower Trail, which is approximately 3.3..