Trail Running calendar near Ashburnham 2026-2027

Experience peak autumn foliage at the Mt. Tom Trail Race featuring a 25k solo or relay, a 10k, and a 5k fun run through rugged Massachusetts state park trails with significant elevation.

Tackle a unique mountain course that goes up and down four times over 4.9 miles. The event offers prize money, age group awards, and benefits the Keene Community Kitchen. Early registration includes a t-shirt.

Rugged 5k trail run, ruck, or walk in Berkley MA on October 25, 2026 with in person and virtual options. Dogs may join on leash with a waiver and proceeds support The Baystate Beagle Club and Give2Those.org.

This fall trail run takes place at Powisset Farm in Dover, MA, featuring four scenic distances through farm and woodland trails. Post-race cider donuts and family activities like pumpkin painting add to the farm atmosphere. It's part of the..

Experience the rolling hills of Willowdale State Forest during this multi-distance trail festival. With options ranging from a 10K to a 100K, runners will enjoy a community-focused atmosphere that supports local land conservation.

Test your endurance at this backyard ultra in Winchendon featuring a 4.1666 mile loop through fields and trails. Choose from the last runner standing format, timed races, or a single lap challenge in a relaxed community setting.

Enjoy a 4 mile run through Mine Falls Park followed by a festive post race party and raffle at Martha's Exchange. Support the Nashua Children's Home in this community event hosted by the Gate City Striders.

TARC Winter Classic in Stoneham offers 8, 32 and 40 mile trail races on the white blazed Skyline Trail with rugged roots, rocks, frequent climbs and Boston skyline views. Expect technical trails, minimal markings and a festive finish.

Celebrate 20 years of festive racing with a unique 3.5 mile cross country run or 2 mile walk through the hilly landscapes of Melrose. Enjoy a pasta lunch and compete for coveted nutcracker awards at this local December tradition.