Trail Running calendar near Hadley 2026-2027

Run the rugged Shawangunk Ridge Trail near Rosendale NY for epic cliff top views across five states. Pick 70 mile, 30 mile or half marathon courses over rocky, technical terrain in this unsupported, self reliant challenge.

Run for The Hills is a 4th annual trail 5K on September 12, 2026 at Oswegatchie Hills Nature Preserve, winding around Clark Pond. Expect exposed rocks and roots on scenic trails while helping support preserve maintenance.

Tackle rugged singletrack and sweeping views at Macedonia Trail Race in Kent CT on September 13, 2026, with 12K, 25K and 50K options. Expect steep climbs up Cobble Mountain, fast descents and a festive finish with post race food and medals.

Join the Charlie Stavros Memorial Beach Run on September 15, 2026 in Westerly, Rhode Island, a free 3 mile beach run honoring a beloved local runner. Enjoy a scenic low tide out and back along Westerly Town Beach with friends and family.

The Vermont 50 offers rugged 50 mile mountain bike and ultrarun courses around Mount Ascutney in West Windsor, Vermont. Held each September, it raises funds for Vermont Adaptive Ski and Sports and includes relays, a 50K and kids activities.

Run the newly restored Moosup Valley State Park Trail in Moosup CT with 5K, 10K and a kids fun run on Sunday September 27, 2026. Postrace medallions or tee shirts, food and drink, leashed dogs welcome, and proceeds benefit the Rotary Club o..

Tackle an Everesting relay across 61+ miles and 29,029 feet of climbing at Mohawk Mountain in Cornwall CT, with a 72 hour window to run, hike or walk. Team up and test endurance on this epic fall challenge.

Iron Hike Fall Double Kuwohi Trail Marathon Plus Relay is a timed 24 hour trail challenge covering more than 28 miles with epic elevation at Mohawk Mountain in Cornwall Connecticut. Choose solo or relay, run, hike or walk and chase a big da..

Take on Flutters and Foliage Endurance Race in Cohoes NY on Oct 3 2026 with 6 hour, 3 hour and 1 hour solo options plus relays and vendors. Family and dog friendly, proceeds support Flutters of Hope and eating disorder services.

Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes wit..

Take on the NipMuck Trail Marathon in Ashford CT on October 4, 2026, a rugged 26.4 miles out and back across rocks, roots, mud and scenic wood bridges. Organized by the Shenipsit Striders, the race supports Connecticut trail stewardship.

Enjoy autumn trails at the Keene Family YMCA Fall Foliage Trail Races on October 4, 2026, with 5K and 10K options around scenic Keene, NH. Run for community impact while enjoying chip timed courses and seasonal views.

Run a point to point ultramarathon on the Midstate Trail across Massachusetts with crossings into NH, RI and CT. Choose 100 Mile, 50 Mile or 50K routes through woodlands, fields and rivers at peak fall.

Take on the Mohawk Mountain Race at Mohawk Mountain Ski Resort with marathon, half marathon, 10K and 5K on challenging ski mountain trails featuring sweeping fall foliage and plenty of climbs and descents. Finishers earn medals and enjoy po..

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

Join a scenic trail run through NE Connecticut along the Air Line State Park Trail with marathon, half, 10K, relay and junior distances. Tackle the Trail supports local students pursuing higher education.

Run the Ghost Train Trail in Brookline, New Hampshire amid peak fall foliage. Choose ultramarathon, relays, haunted 30 mile night or 15 mile race and help fund local conservation and trail preservation.

Late autumn weekend at Red Wing Recreation Area with looped 100k, 50k and 10k races over rugged, hilly trails. Expect big elevation, full aid, camping for 50k runners and finisher awards, with UTMB Index status for longer distances.

Run a scenic loop of single track and rolling farm trails at Gurski Farm in Brookfield, where the 4 mile course brings you past fellow competitors again and again. Choose 8 hour, 4 hour, 5K or 5K Canicross with medals and food.

Tackle scenic but rugged trails at Tarrywile Park in Danbury with 10K, half and marathon options offering sweeping views of the park and lakes. Expect technical single track, steep climbs, finisher medals and hearty post race snacks.