Trail Running calendar near Pittsfield 2025-2026

The Flutters and Foliage Endurance Run is an annual fundraising event held in Cohoes, NY, organized by Flutters of Hope Inc., a nonprofit supporting individuals and families affected by eating disorders. This year marks its third edition, featuring various endurance challenges, including a 6-hour ru..

The NipMuck Trail Marathon is a challenging 26.4-mile race held on the scenic Nipmuck Trail in Ashford, Connecticut. Participants can choose between the full marathon or a relay option, where two runners share the distance. The course features a mix of terrain, including rocks, roots, and mud, makin..

The Midstate Massive Ultra Trail is an endurance running event taking place in New Ipswich, New Hampshire, featuring three challenging race options: 100-mile, 50-mile, and 30-mile courses. Set against the stunning backdrop of autumn in New England, the race follows the historic Midstate Trail, cross..

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 is an exciting running event set against the stunning backdrop of Mt. Tom, featuring challenging terrain and breathtaking views, particularly during peak foliage.Participants can choose from a solo 25k, a 2-person 25k relay, or a solo 10k. The race supports the Kestrel Land Tr..

The Fall Back Into The Trails Series is an annual running event hosted by C.T.W Endurance, taking place at the Red Wing Recreation Area in Lagrangeville, NY. Scheduled for November 1-2, 2025, the series features three race options: a challenging 100k, a 50k, and a 10k, each with varying elevation ga..

The Moreau Half is an exciting 14-mile trail race set in the scenic Moreau Lake State Park, scheduled for November 1, 2025. This challenging event features a course that includes approximately 2,700 feet of elevation gain, making it suitable for experienced runners. Participants can expect a technic..

The Saratoga Stryders Fall Back 5 Mile Trail Race is an exciting running event set in the scenic Saratoga Spa State Park. Participants can enjoy a challenging course that features a mix of hills, ridges, and single-track trails, showcasing the park's natural beauty. The race encourages runners to em..

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 event features a scenic, approximately 4-mile loop course that includes single track and rolling farm trails, fostering a vibrant community atmosphere am..

The Tarrywile Half Marathon is a challenging trail race set in Tarrywile Park, Danbury, Connecticut. Known for its tough terrain, the course features significant elevation gain of nearly 3,000 feet and technical Northeast single track paths. Participants can choose from three distances: a Half Marat..

The Fall Fling 400 is an annual trail running event organized by the CT Trailmixers, featuring a unique 400-minute race where participants can complete as many loops as they wish on a two-mile course. Additionally, a 4-mile option is available, consisting of two laps of the same course. The event pr..

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 Sleeping Giant Trail Runs is a challenging new race set in one of Connecticut's iconic parks, known for its diverse trails. Participants can choose between a 25K and a 50K course, both featuring over 3,000 feet of elevation gain. The event showcases a mix of smooth carriage roads and technical,..