Trail Running calendar near New Boston 2026-2027

The Cranmore Mountain Race is a classic two lap mountain run in New Hampshire. Runners tackle ski slopes and trails for a share of $7500 in prizes. This historic event is part of the USATF New England Mountain Circuit.

Distances & Overview The event offers two distances: a 10-mile trail race and a 50-kilometer (50K) trail race. The 10-mile course is a single loop, while the 50K course consists of three loops of approximately 10 miles each. Both races..

Run a scenic autumn 5k trail through Wrentham conservation land and a working farm. This cup-less race supports local agriculture and includes family Halloween fun. It's the final event of the Farm to Trail 5K Series.

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.

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..

The Holistic Hustle offers a 5K, 10K, and a kids' fun run at Kennebunkport's Emmons Preserve. All finishers get a unique wood-burned medal, and the event features music, games, and refreshments. Proceeds support holistic education.

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.

Race Mozey brings the Central European Krampus Run tradition to New England. Choose from a 5K, 10K, or a 9-hour challenge to complete laps at the Dartmouth Skiway. Finishers get medals, and the event supports Vermont Adaptive Ski and Sports..

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.

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.