Trail Running calendar near Pittsfield 2026-2027

A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.

A community 5K in Jaffrey, NH offering a woods trail and a rail trail out and back. Proceeds support the volunteer Jaffrey Firefighters Company and equipment needs of the Jaffrey Fire Department.

A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.

An 8.5 mile loop at Merck Forest with about 1,800 feet of climbing, two aid stations, and a 0.75 mile kids loop around the farm. Packet pick-up is available in Manchester and at the Sap House start area.

A point to point 26 miles trail race in the Slide Mountain Wilderness near Shandaken, NY, featuring nearly 7,000 feet of vertical gain and technical, rocky terrain. Proceeds support Run Wild, Inc and several race services are provided.

A trail running event in Gardiner, NY offering a 5 km run, an optional 10 km two-lap route and a 200 yard kids run, with pre registration T shirt incentives and a sneaker recycling program.

Experience a massive endurance test at Mohawk Mountain Ski Area. This ultra trail event features a 152 mile course with over 72,000 feet of elevation gain to be completed within 84 hours.

A 24 hour trail event at Mohawk Mountain Ski Area in Cornwall Connecticut featuring a Double Kuwohi route of about 28 miles and 13,685 feet of elevation. Participants may run, hike, or walk.

An October endurance race in Cohoes, NY offering timed 1-, 3- and 6-hour solo and relay options. The event benefits Flutters of Hope, a nonprofit supporting individuals and families affected by eating disorders.

A 50 kilometer trail ultramarathon around Lake George starting and finishing at Camp Chingachgook in Kattskill Bay. The course climbs about 9,000 feet and crosses four peaks; prior ultra trail experience is required and registration closes..

A 26.4 mile trail marathon on Connecticut’s Nipmuck Trail featuring rocks, roots, mud and wood bridges, with an optional two-person relay and elapsed time cutoffs. Organized by the Shenipsit Striders in Ashford, CT.

Keene Family YMCA Fall Foliage Trail Races feature 5K and 10K trail courses starting and finishing at the Keene YMCA, with chip timing, age-group prizes, and proceeds supporting YMCA programs and access.

A fall trail race day in Norfolk, CT offering 5K, 10K and a half marathon with steep climbs, private-trail sections, a cupless policy with water stations, and on-site food and beverage vendors.

Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.

Experience a trail race at Mohawk Mountain Ski Resort featuring distances from 5k to a full marathon. Run through fall foliage on a course that includes steep ski slopes and the scenic Mohawk State Forest.

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All proceeds support local trail maintenance.

A fall trail race at Mt. Tom State Park on October 24, 2026, with single and relay options from 5k to 25k on rugged single-track terrain. The event supports Kestrel Land Trust and includes aid stations, medical crews, and awards.

A community trail event at Ives Farm featuring a 5K trail race, a youth team relay, and a free kids Pumpkin Dash, plus family activities and proceeds supporting local YMCA and land trust projects.