Trail Running Calendar Connecticut 2025-2026

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 People's Forest 7-Mile Trail Run is an annual trail running event held in Barkhamsted, Connecticut. It features a challenging 7-mile course through scenic forest trails, offering runners a chance to experience natural beauty and varied terrain. The race is part of the USATF Connecticut Mountain..

The Tappen Brook 5K, held in Bridgewater, Connecticut, is an annual trail running event hosted by the Bridgewater Land Trust and the Bridgewater Recreation Commission. Set in the scenic Bridgewater Town Park, the course features newly developed trails winding through forested woodlands with gentle h..

The Stonington Cross Country 5K is a free running event held at Stonington High School in Pawcatuck, Connecticut. The course begins with a loop on the school track, followed by a half-mile run on quiet, dead-end streets within the campus. Runners then transition to a mix of single- and double-track..

The Shenipsit Striders 50th Fatass is a celebratory running event held at Crandall's Park Pavilion in Tolland, Connecticut. Marking the club's 50th anniversary, the event features an 8-hour window where participants run multiple 5K loops on a trail course starting and finishing at the pavilion. Runn..

The Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, traversing the state north to south along the scenic and flat Farmington Canal Heritage Trail. Starting in West Suffield and ending at New Haven harbor, the course passes throu..

The Macedonia Trail Race, held in Macedonia Brook State Park in Kent, Connecticut, offers a unique trail running experience with lush single-track forest trails, challenging climbs and descents, and stunning viewpoints including Cobble Mountain with views of the Catskill Mountains. Now in its 7th ye..

The Storybook Half Marathon is a scenic 13.1-mile trail race held in Roosevelt Forest, Stratford, Connecticut. The course consists of eight loops on a 1.64-mile wooded trail featuring singletrack and doubletrack paths with roots, rocks, and gentle hills, offering a charming yet moderately challengin..

Run for the Hills is an annual 5K trail run and walk held at the Oswegatchie Hills Nature Preserve in Niantic, Connecticut. The event offers participants a scenic course around Clark Pond and through over 450 acres of coastal forest, showcasing the preserve's natural beauty. It serves as a fundraise..

The Angevine Farm Trail Festival, held annually in Warren, Connecticut, offers a scenic and challenging trail running experience in the Northwest corner of the state. The event features multiple distances including a half marathon, an 8-hour endurance race, a 5K, and a 5K Canicross (running with dog..

The Cockaponsett Trails to a Cure is a trail running event held in Chester, Connecticut, within the Cockaponsett State Forest. Participants can choose between a 4-mile or a 9-mile race, with the shorter distance comprising the first part of the longer course. The trail features natural terrain inclu..

The IronHike Endurance Series, held at Mohawk Mountain Ski Area in Cornwall, Connecticut, is a multi-day endurance event featuring rugged, scenic courses designed to challenge participants with significant elevation gains. Spanning from October 2 to 5, 2025, the series offers various timed events ra..

The NipMuck Trail Marathon, held in Ashford, Connecticut, is a challenging 26.4-mile trail race along the scenic Nipmuck Trail. The course features diverse terrain including rocks, roots, mud, and wood bridges, with a route that heads south to Route 44, returns to the start, then goes north to Bosto..

The Norfolk Land Trust Trail Race Series, including the Haystack Mountain Challenge, is held annually in Norfolk, Connecticut. The event features three trail races: a 5K, 10K, and a challenging half marathon. The 5K course runs through scenic Barbour Woods with a mix of single and double track trail..

The Forbidden Forest 30 Hour Ultra Run is an epic endurance event held in Stratford, Connecticut, offering runners up to 30 hours to complete distances ranging from a marathon (26.2 miles) to 100 miles or more. The course features a challenging 2.23-mile loop with roots, rocky terrain, and a notable..

The Mohawk Mountain Race, held at Mohawk Mountain Ski Area in Cornwall, Connecticut, offers a challenging trail running experience with 5K, 10K, Half Marathon, and Marathon distances. The course features steep ascents and descents on ski mountain trails, including the Wildwood, Timber, Pine, Laurel,..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 26 miles.

The Bimblers Bluff 50K is an off-road ultramarathon held in southern Connecticut, starting at Guilford Lakes School. The course traverses several interconnected woodland preserves, featuring rolling forest roads and single-track trails that can be extremely rocky. Unlike many ultras, the route does..

8 Hours at the Farm is a trail running event held at Gurski Farm/Williams Park in Brookfield, Connecticut. The race features a rolling country course with an approximately 4-mile loop combining single track and farm trails, offering a scenic and community-focused atmosphere. Participants can choose..

The Tarrywile Half Marathon, held in Danbury, Connecticut's Tarrywile Park, is known as one of the toughest trail half marathons in the region. Covering nearly 3,000 feet of elevation gain, the course features technical Northeast single-track trails with rocky, rooty, and hilly terrain. Runners enjo..