Trail Running calendar near Great Barrington 2026-2027

Charity 5K run and 1.5 mile walk in Huntington MA on a mixed pavement, field and trail course that finishes at Littleville Dam.

An obstacle-based 5K at Short Beach, Stratford on September 12, 2026, with 18+ obstacles and fundraising for the Sterling Community Center.

Trail races of 70 mile, 30 mile and half marathon distances along the rugged, largely unsupported Shawangunk Ridge near Rosendale NY.

A 56 mile end to end run along the Farmington Canal Heritage Trail from West Suffield to New Haven raising funds for Mental Health Connecticut.

A Keene State College alumni cross-country meet on 09/12/2026 at the Keene State Athletic Complex featuring a men's 5K and a women's 2 Mile race; registration runs 09/06 to 09/12 with a $25 fee per event.

Pittsfield State Forest trail races on September 12, 2026 offering 50k, 25k, 15k and a new 5 mile option on a double-loop course with three aid stations.

Experience a fun inflatable obstacle course at Butterfield Park. This 1 mile run or walk supports 6th grade students at Fisher Hill School in reaching their educational trip goals through community participation.

Trail race in Macedonia Brook State Park, Kent CT offering 12K, 25K and 50K loop courses with significant elevation, aid stations, and a cupless policy.

Pisgah Mountain Trail Races in Chesterfield, NH offers 50k and 23k mountain trail ultraruns on Sunday 9/13/26. Aid stations provide LMNT, Tailwinds, and Untapped and proceeds support New Hampshire Special Olympics.

Timed trail races in Pawling NY offering 24, 12, 6 and 3 hour options on an approximately 1.68 mile loop with on course aid and athlete camping.

A community trail run and walk on September 19, 2026 at Huyck Preserve offering 2, 5, and 8 mile routes through lake, historic track, and waterfalls, with proceeds shared by the Huyck Preserve and Rensselaerville Library.

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 run and a children’s 1 mile fun run at Schodack Town Park on September 19, 2026, raising funds for Hope House. Entry fees include 5K $30 and children free with parents running $30.

Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.

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.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.

A fall trail race at Merck Forest and Farmland Center featuring an approximately 8.5 mile loop with about 1,800 feet of climbing and two aid stations. A separate 0.75 mile kids loop circles the farm and allows parent participation.

A women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026. The course has 18+ obstacles, welcomes participants ages seven and up, and emphasizes teamwork over competition.

A timed charity tower climb at Empire State Plaza in Albany that reaches the 42nd floor with 809 steps. Water stations, bailout floors and medics are provided; registered participants receive a t shirt and finisher's medal.

Point to point 26 miler in the Slide Mountain Wilderness with nearly 7,000 feet of vertical gain and multiple aid stations; proceeds support land conservation.