Trail Running calendar near Hamilton 2026-2027

A five mile fun run along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on June 13, 2026. The day features food and festivities, a children's loop, return transport on request, and benefits local historical socie..

A second annual trail event in Dunstable, Massachusetts offering a 5 mile loop or a six hour race of repeated 5 mile loops. The course follows an old railroad bed, an arched stone bridge, woods, peaks, and single track trails.

A community fun run on 06/13/2026 behind Madbury Town Hall with a 1K kids run and a 5K route through Kingman Farm trails. Registration is free and donations for park improvements are accepted on the day.

A family-friendly three-loop course of about 5 km through Natick Community Organic Farm with mixed trail, field and road surfaces. All participants receive a chicken medal and proceeds support the farm’s education and teen programs.

A 5.6 K trail run and walk at Berry Pond in Harold Parker State Forest on June 14, 2026. Walkers and leashed dogs are welcome; prizes are awarded, all entrants receive a bandana, and hotdogs are provided after the race.

Teams are driven blindfolded several miles to an unknown location, then must navigate back to the start by the shortest route. This free team event uses cross country scoring and prohibits GPS, phones, and running on I 95 or I 495.

Trail races at Dublin School Outdoor Center on June 20, 2026 feature a 10K and a half marathon with significant elevation gain, technical trail sections, and views of Mount Monadnock.

A trail half marathon in Lynn Woods Reservation on June 21, 2026, run as three identical loops over forested singletrack and carriage roads. The event emphasizes environmental stewardship and uses a centralized start and finish at the main..

A women only 5K obstacle mud run at Kimball Farm in Haverhill, MA on June 21, 2026. The course features 18 plus obstacles and welcomes participants age 7 and up with an emphasis on fun and teamwork rather than competition.

Three summer trail races at West Hill Dam in Uxbridge, MA, with well-marked wooded single and double-track courses, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

A small weeknight trail race series around Portland, Maine offering four community focused events with courses from about 5K to 6.5 miles. Fields are capped at 75 runners and series awards recognize overall top finishers.

A Spartan obstacle weekend at Carter and Stevens Farm in Barre Massachusetts featuring a 5 km Sprint, a 10 km Super, kids races, and an obstacle workshop across mud, woods, and rolling hills.

Second annual Kennebec Savings Bank East Bayside Trail Fest in Portland on June 28 2026 offers three trail events plus a post event celebration with music, food trucks and local beer. Proceeds support Portland Trails and the Bicycle Coaliti..

A backyard ultra on Portland's Back Cove Trail featuring repeated 4.16 mile loops along a tidal estuary. Two aid stations, on site personnel, free adjacent parking, and volunteer support are provided; refunds are restricted.

A looped trail ultramarathon in Northfield, NH on July 11, 2026, the Spaulding Woods 50K runs five 10K singletrack loops with aid stations, a ten hour finish limit, and an eight hour cutoff to start the final loop.

A 12K trail race on the Blue Hills Skyline Trail with about 2,300 feet of climbing, rocky steep terrain, and minimal aid. The route follows Skyline blazes from the Blue Hills Ski Area parking lot and requires participants to carry hydration..

A memorial 5K run and walk at Owen Bell Park in Dayville CT that raises funds for a scholarship for Killingly Ag-Ed seniors. The day includes a 5K, a walk, and a kids fun run on off-road paths with possible trip hazards.

A 12 hour trail event in Lawrence Woods, Middlesex Fells Reservation near Medford MA on July 18, 2026. The course is a roughly 5 mile loop with a minimal aid station and parking at the nearby high school lot.

A roughly 3.8 mile trail race at Kingman Farm in Madbury, NH on July 26, 2026, featuring rolling nordic style paths and switchback singletrack; proceeds support the Doug Flutie Jr. Foundation for Autism and day of registration is available.

A community trail run in Bedford, New Hampshire on July 30, 2026 featuring a 5 km course with age-based categories and fees, online registration with a noon deadline, and options to donate or buy merchandise to support the Rotary Club of Be..