Trail Running calendar near Hamilton 2026-2027

A mountain trail race in Keene NH on October 25, 2026 covering 4.9 miles with 1,650 feet of elevation across four laps; the event benefits the Keene Community Kitchen and offers prize money, age-group awards, and raffles.

A fall trail 5k in Berkley MA combining running, rucking, and walking to honor military, first responders, and K9s. Dogs are allowed on leash with a waiver and proceeds support local canine and service organizations.

A fall trail race at Powisset Farm in Dover on October 25 2026 offering four distances, one water aid station, post race cider donuts and family activities with awards for top finishers.

A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.

A stair climb at Gillette Stadium where participants walk, jog or climb around the lower bowl while music and team highlights play. Net proceeds support Homes for Our Troops.

Discover the beauty of Emmons Preserve at a community event featuring trail races and family activities. Enjoy music and local treats while supporting holistic education through a variety of distances for runners and walkers.

A Stadion 5K obstacle race at Fenway Park on November 7-8, 2026, featuring 20 obstacles and a finish across home plate. The weekend also includes a 1 to 1.5 km kids race, spectator tickets, team options, and a service member discount.

A multi hour loop event on the New Boston Rail Trail near the fairgrounds offering 6, 12, 24 and 30 hour individual and relay options, chip timing, a central aid station, team entries, pacer rules and 100-mile buckles.

A November trail festival at Willowdale State Forest in Ipswich offering multiple looped distances from a 10K to 100K, a Cider Donut Mile, and a flagged 0.5‑mile youth run, with cupless aid stations and fundraising for local land trusts.

A backyard ultra at Kenty's Farm on November 7, 2026 where runners complete repeated 4.1666 mile laps until one remains; also offers 6, 12 and 24 hour timed options and a single-lap competition.

Looped trail event at White Barn Farm featuring a clearly marked 3.1 mile loop and a fully stocked aid station. Participants stack laps to reach distances from 5K up to 50K, with each completed loop recorded.

Trail races in Upton State Forest include a 10.5K loop and a 13.1 mile half marathon run as two laps. Aid stations are spaced about every 3 miles and post race offerings include fire pits, hot soup and hot chocolate.

A 6 hour timed trail race on a 5K loop at Wright Locke Farm in Winchester Massachusetts, featuring rocky rolling singletrack, a barn aid station in a cupless format, and provisions for adaptive athletes and youth discounts.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

A trail running event in Stoneham MA on December 5, 2026 offering 40 mile, 32 mile and 8 mile distances. Online registration opens August 1, 2026 and donations will support Friends of the Fells and entry fee scholarships.

Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.

Experience the US Snowshoe Nationals in Concord New Hampshire. This winter event features 5k and 10k races on a flat and fast course through open fields and singletrack trails.

Trail races at Monastery Trails in Cumberland, RI on March 14, 2027 offer distances from a 1 mile kids run to a 100K 12 hour ultra. Team ultra entries and a multilap 5 hour option are available and all finishers receive a medal.

A point to point 123 mile ultramarathon across Connecticut from East Thompson to Southport with trail and road sections, a 36 hour cutoff, relay options, and staffed aid stations.