Trail Running calendar near Great Barrington 2026-2027

A third annual trail event on October 10, 2026 in Wilton, CT featuring a 5K trail race and an accessible short run/walk, event T-shirts, food and on-site access to farm grounds; proceeds support employment opportunities for people with disa..

Community 5K and a 0.5 mile youth run at Pitney Meadows Community Farm on October 10, 2026. The mixed surface, spectator friendly course runs on grass and stone dust and raises funds for the farm's programs.

Experience a scenic 5K run on the historic carriage roads of Rockefeller State Park Preserve. Support trail maintenance while enjoying autumn views of Swan Lake and rolling pastures.

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.

A pickle-themed Halloween obstacle event in Wallkill, NY with an adult 5K and a 1K kids course, themed medals, costumes, mud, and a community-focused Donate a Dragon 3D printing project.

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.

HHNC Meadows & Trails 5K is an off road 5K at Hudson Highlands Nature Center in Cornwall NY on 10/17/2026, featuring meadows, ponds, wooded trails and views of Black Rock Mountain. Entry is $35 and children under 18 run free.

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.

An off-road *50K* through interconnected woodland preserves in Guilford, Connecticut, featuring rocky single track and rolling forest roads. The course is set for experienced trail runners and has limited entries.

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 run at Ives Farm hosted by Cheshire Community YMCA and Cheshire Land Trust. Features a trail 5K, a youth Y Cup relay with elementary teams, a free Pumpkin Dash for young children and family fall activities.

A trail event at Muscoot Farm on October 25, 2026 featuring a 5 mile race plus two kids courses for ages 7 to 12 and 6 and under. Packet pickup and parking are provided and participants receive Farm Bucks and kids medals.

A 4.9 mile mountain trail race in Keene, NH on October 25, featuring four up and down laps on different trails, 1650 feet of elevation, prize money and age group awards, with proceeds supporting the Keene Community Kitchen.

Trail half marathon, 5K and a kids fun run in Garrison, NY on October 25, 2026, benefiting the Friends of Philipstown Recreation. The courses run through Hudson Highlands State Park and pass Osborn Castle on private property reserved for re..

Tri-State New York Spartan Event Weekend at Sunflower Valley Farm offers Sprint, Super, Kids races, Hurricane Heat formats, and spectator access with courses through woods, fields and creek runs featuring mud and Spartan obstacles.

A trail running event at Red Wing Recreation Area near Lagrangeville, NY, offering 100k, 50k and 10k looped courses with on-course aid, finisher medals and awards for top male and female finishers.

A trail half marathon at Moreau Lake State Park in Gansevoort, NY, covering roughly 14 miles with about 2,700 feet of elevation gain on technical singletrack. The course is fully marked with one aid station and parking at the park beach.

Experience a unique timed trail event at Gurski Farm featuring a four mile loop of rolling farm trails and single track. Choose between eight hour, four hour, or 5K options in a community focused environment.

A 10K trail race in Penwood State Park featuring technical single track on the Metacomet Trail and rocky runnable terrain. No aid stations so runners must carry hydration for 6.2 miles; proceeds partly support NAMI.