Trail Running calendar near Springfield 2026-2027

An obstacle based 5K at Short Beach in Stratford CT featuring more than 18 obstacles and a family friendly course. Proceeds support the Sterling Community Center including the food pantry and youth programs.

A trail event along the 70-mile Shawangunk Ridge near Rosendale, NY, offering 70-mile, 30-mile, and half-marathon routes across varied terrain. The course is minimally supported and uses shuttles with Rosendale-only parking.

A charity 56 mile end to end run along the Farmington Canal Heritage Trail from West Suffield to New Haven. The unsupported group event raises funds for Mental Health Connecticut and requires self support and a 14 hour completion limit.

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.

A trail running event in Pittsfield State Forest offering 50K, 25K, 15K and 5 mile options on a double-loop course with significant climbing; proceeds support Free to Run, Inc.

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.

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.

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.

GBTC XC Invite in Carlisle, MA features youth and Open/Masters cross-country races at Great Brook Farm State Park on September 13, 2026. Distances include a 2K youth race and multiple 5K races; registration runs August 1 to September 11.

A free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.

A timed trail festival in Pawling, New York offering 24 hour, 12 hour day and night, 6 hour and 3 hour races on a short mixed surface loop with aid stations, crew areas, finisher medals, and distance based awards.

A trail-based 5K run/walk and a 3K walking route at Mine Falls Park supporting Meals on Wheels of Hillsborough County, with a $30 registration and a 2026 event T-shirt for early registrants.

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 one mile obstacle course in Warren, RI with two giant mud pits, kids play area, food and giveaways. Proceeds support Thrive Outside and its programs to expand youth access to nature.

An 18 mile out and back trail race in New Ipswich, New Hampshire, climbing toward Watatic Mountain Reservation with technical, rugged single-track terrain. Registration opens June 15 2026 and the fee is $55.

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.