Trail Running Calendar Connecticut 2025-2026

The Centurion Ultra Trail Event is a challenging running competition set in the picturesque Roosevelt Forest in Stratford, Connecticut. Scheduled for June 28-29, 2025, this event features multiple race options, including 100 miles, 100K, and 50 miles, with a unique loop course of 2.5 miles. Particip..

The 7-11 Slurpee Day Ultra 60k is a unique running event taking place on July 11, 2025, in Connecticut. Participants will cover a self-supported distance of 37.5 miles, stopping at various 7-11 locations along the route. The event encourages a fun and relaxed atmosphere, with no strict course or pac..

The Soapstone Assault is a challenging approximately 5-mile trail race held at Soapstone Mountain, featuring a unique course that requires participants to climb the mountain six times. This event is designed for those seeking a rigorous hill workout, as runners navigate steep, rocky, and potentially..

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 and lush forest trails. Participants can choose from three distances: 12K, 25K, and 50K, each featuring challenging climbs and breathtaking viewpoints. The 25K..

The Storybook Half Marathon is a friendly and inclusive running event taking place in Stratford, CT, on September 13, 2025. Participants can choose to run, jog, hike, or walk the scenic trail course, which features a mix of single and double track trails with some elevation. The event allows up to f..

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. This annual event features a variety of races, including an 8-hour challenge, a half marathon, and a 5K, with routes that traverse grassy fields, state forest trail..

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, Connecticut, 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, i..

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 Bimblers Bluff 50K is an off-road foot race held in southern Connecticut, starting at Guilford Lakes School. The course features rolling forest roads and rocky single tracks, providing a challenging experience for runners. Unlike many similar events, participants do not complete the same loop mu..

The "8 Hours at the Farm" event, organized by Steep Endurance, takes place at Gurski Farm/Williams Park in Brookfield, CT. This trail running event features a scenic 4-mile loop with a mix of single track and rolling farm trails, fostering a vibrant community atmosphere among participants. Runners c..

The Tarrywile Half Marathon, scheduled for November 16, 2025, is a challenging trail race set in Danbury, Connecticut. Known for its tough terrain, the course features significant elevation changes and technical single-track paths, offering stunning views of the surrounding area. Participants can ch..

The Tower Tag Challenge is an exciting trail running event held at Sleeping Giant State Park in Connecticut, known for its stunning views and diverse trails. Participants can choose between 4-hour and 8-hour options, racing up and down the Tower Trail, which ascends over 600 feet to the Observation..

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..