Trail Running calendar near Pittsfield 2026-2027

A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.

A repeated 3.3 mile out and back on the Tower Trail at Sleeping Giant State Park, with four hour and eight hour options and a cupless aid station at start and finish.

A 16 mile out-and-back trail race on the Nipmuck Trail near Bigelow Hollow State Park in Union CT with technical terrain, minimal aid, and proceeds supporting local trails.

A 123 mile point to point ultramarathon from East Thompson to Southport, CT offering solo 200k and 100k options plus team relays. The mixed trail and road route has a 36 hour cutoff with staffed aid stations and medical support.

Trail races on a 25K loop at Sleeping Giant State Park featuring technical singletrack, steep rock scrambles, and an optional second loop for the 50K.

Looped trail races of 17K and 50K at Penwood State Park, featuring rocky single track on the Metacomet Trail and a nine hour cutoff for the 50K.

A mountain trail run in Ellenville, NY on April 24, 2027 offering a 25K (about 17 miles) and a 10 mile course across technical singletrack, cliffs and carriage roads, with aid stations and support for land conservation charity Run Wild, Inc..

A mountain trail event in the Shawangunk Ridge near Ellenville offering a 25K (closer to 17 miles) and a 10 Miler on technical singletrack and carriage roads, with significant climbing, marked courses, two aid stations, and proceeds support..

A 50 mile ultra, a 26.2 mile trail marathon, and relay options on the Shawangunk Ridge to raise funds for Mohonk Preserve.

Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.

A trail running event on the Wapack Trail in Ashburnham Massachusetts with 21.5 mile, 43 mile, and 50 mile options across rocky, technical terrain with aid stations, drop bag support, and a manual timing system.

A technical trail event near Beacon, NY offering a roughly 14.5 mile half and a 26.5 mile full with large elevation gain, exposed climbs, staffed aid stations, post race food, a shirt and a finisher item.

A community 5K in Ellenville starting and finishing at Aroma Thyme Bistro, with a course along the base of the Shawangunk Mountains and a stretch on the newly resurfaced Rail Trail. Proceeds benefit local food pantries and youth scholarship..

Point-to-point trail runs of 112 or 50 miles along the New England Trail blue blazes to Guilford, CT, requiring dedicated crews, navigation, and night trail experience.

A mountain trail event in Roxbury NY on June 6, 2027 featuring a 6.5 mile course with 3500 ft of ascent and a steep 5k with a downhill finish. Organized by CTW Endurance with awards and finisher swag planned.

A two day Spartan obstacle event at Carter & Stevens Farm near Barre MA featuring Sprint 5 km, Super 10 km and kids races across wooded trails and open pastures.