Trail Running calendar near Sterling 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.

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.

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.

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 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 from Windblown Ski Area in New Ipswich NH to Watatic Mountain in Ashburnham MA with steep technical terrain and a three hour turnaround cutoff.

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.

The Arc'teryx Run Boston will take place in Milton on Sunday 20 September 2026. You can run 10 kilometers.

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 5K trail race at Goddard Park in Warwick, RI on September 26, 2026, over fields and wooded trails along Greenwich Bay with onsite parking and age-group awards.

Technical trail races in Burlington CT on the Tunxis Trail offering 8K and 5K courses that pass the CT State Trout Hatchery and Nassahegan State Forest.

A trail event on the Moosup Valley State Park Trail featuring 5K, 8K, 10K and a Kids Fun Run. Parking and the finish are at Weidele's Pizza with post-race food, awards and a medallion or shirt option.

Trail races at the Assabet River National Wildlife Refuge in Sudbury MA include a 10K, a 30K and a 6 hour timed event. The course uses dirt and gravel double track trails with two aid stations and cupless fueling.

Run for Nature on September 27, 2026 at Shedd Park in Lowell offers 5K, 10K and a 1 mile kids run to support local conservation and education.