Trail Running calendar near Great Barrington 2025-2026

Join a friendly, informal 5 to 10k run or snowshoe on a roughly 10k course with loaner snowshoes available. Bring a spare pair to share, enjoy light refreshments, and team up for bragging rights and a shared baked treat.

Join the Frozen Heart 900, a free grassroots winter loop in Rockfall CT where runners take on a 15 hour challenge around a 2.2 mile trail loop. Self supported format with a heated meeting room for warming, so bring headlamps and carpool.

Test your trail skills on the Northern Nipmuck Trail Race, a rugged 16 mile out and back through Yale Myers Forest and Boston Hollow with technical terrain and serious climbing. Limited to 100 entrants, proceeds support local trails.

Tackle rugged singletrack and steep rock scrambles at the Sleeping Giant Trail Runs in Hamden CT on March 29, 2026. Choose a challenging 25K loop or a double 50K and enjoy aid stations, medals and post race food and drinks.

Tackle technical, rugged trails and steep climbs at Big Bear Squatch North in Bear Mountain NY on April 4, 2026. Choose a challenging 10K or a grueling half marathon, with proceeds supporting the New York New Jersey Trail Conference.

Run a scenic quarter marathon at West Hartford Reservoir on April 11, 2026, as the Hartford Track Club hosts a small, timed field limited to 150 runners. Enjoy chip timing, post race treats and a friendly, looped trail course.

Join the John Jay Community Trail Race in Cross River NY on Sunday April 12, 2026 for a family friendly outing with a 5k, 4k Jay Walk and a 200 meter Kids Dash. Race on scenic wooded, hilly school trails and finish at the track.

Tackle wooded trails at the Farm & Forest All Terrain 5K and Hog Wild Kids Fun Run in Stamford, CT on April 12, 2026. Family friendly and community focused, this race raises funds for the Stamford Museum and Nature Center.

Take on rugged Traprock at Penwood State Park in Bloomfield CT on April 18, 2026 with 17K one loop or 50K three loop options. Expect rolling, technical single track and rocky trails; bring your own cup for this cupless, chip timed race.

Run the Brooklyn Cider House Spiked Apple 5k in New Paltz on April 19, 2026 for a chip timed 5K through cider country. Enjoy a homemade cider donut, a pour of cider and a finisher medal that doubles as a bottle opener.

Squatchywaska Mountainfest in Ellenville offers adventurous 25K and 10 Mile trail runs on the Shawangunk Ridge with steep climbs, technical singletrack, and stunning views. Entry is capped at 150 and proceeds help protect Verkeerder Kill Fa..

Join the Lake Mohegan Women’s Trail Race at Lake Mohegan in Fairfield CT for 5K, 10K or a 4 hour loop challenge open to women and non binary runners. Enjoy scenic trails, finisher medals, post race snacks and a welcoming community vibe.

Run the 52nd Jack Bristol Lake Waramaug Ultra Races on April 26, 2026 in Kent CT with 100K, 50 mile and 50K options around scenic Lake Waramaug. Flat rolling loops, four aid stations and finisher swag make this a rewarding spring ultra.

Enjoy a spring 10k trail race in Cross River, NY on April 26, 2026, winding through scenic park trails. Entry is by lottery with registration opening January 2, 2026, perfect for trail runners seeking a well organized challenge.

Tackle the scenic Seven Sisters Trail Race in Amherst, MA on May 2, 2026, an out and back along the Holyoke Range ridgecrest. This rugged 12 mile course delivers steep climbs, rocky singletrack and over 3,500 ft of elevation for a thrilling..

Join A Run to Remember on May 2 in Red Hook and run or walk scenic farm trails through meadows, orchards, and woods at Greig Farm. Honor loved ones, celebrate community spirit, and vie for cash prizes in the 5K and 10K races.

Take on Breakneck Point on May 3, 2026 in Beacon, NY with a rugged half or full ultramarathon featuring huge elevation and technical single track. Expect steep exposed climbs, aid stations, and a finisher shirt and memento.

Blue 2 Blue Challenge is a rugged 50K through New Haven trails, with about 6350 ft of climbing and technical rocky terrain including a summit at Mt Sanford. Expect a cutoff driven, no frills race for seasoned trail runners.

Take on the Dandelion Dash 5K or the Mushroom Mile on The Hartsbrook School trails, with a virtual option available. Muddy, scenic terrain and proceeds support the school's Land Stewardship program.

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.