Trail Running Calendar Massachusetts 2026-2027

A memorial 5k trail run and walk in Kingston, MA on March 14, 2026 that raises funds for a scholarship established by the participant's family. First fifty entries receive a t-shirt and all proceeds support the scholarship.

A Trail Animals trail event at Hale Education in Westwood offering a timed six hour option and a 3.5 mile singleloop on mostly singletrack around ponds. One cupless aid station at start/finish and limited parking with possible walking.

The Tortoise and the Hare Trail Races feature a timed 10K, 5K, and a fun 1-mile color run in Salisbury, MA. This annual fundraiser for local parks draws a crowd of about 500 participants. Runners can enjoy trail courses, post-race refreshme..

This USATF-sanctioned 10-mile trail race runs along the Merrimack River in Andover, MA. The event features unique homemade prizes and awards, with proceeds supporting local trail maintenance. Post-race refreshments and a raffle add to the c..

Shake off winter at the Spring Fever trail run in Wompatuck State Park. Choose from a 5K, 5M, or 8-hour ultra on a reversed course. All finishers get a custom award and can enjoy on-course support.

The 11th Annual F.O.R 5k Trail Race takes runners through the scenic McDonald Nature Preserve in Wilbraham. This family-friendly trail run supports the local parks' maintenance fund.

A trail race at Jericho Town Forest (Weston, MA) on April 25, 2026 offering 10K, half, marathon, and 50K options on a marked 10K loop, cupless aid station, strict cutoffs, and parking by volunteers.

Experience three seasons of trail running and walking through scenic conservation land and a working vegetable farm in Wrentham with this unique 5K triple series.

The Radish Rambler 5k is a trail run, walk, or hike through scenic conservation land and White Barn Farm in Wrentham. Held on April 25, 2026, it kicks off the farm's season and the Farm to Trail Series. Proceeds support local agriculture an..

A 12 mile out and back trail race on the Holyoke Ridge near Amherst MA featuring technical singletrack, over 3,500 feet of ascent, a 500 runner cap and a waitlist when full.

Take on the trails at the Hartsbrook School for the Dandelion Dash 5K or the family-friendly Mushroom Mile. This community event supports the school's unique Land Stewardship program. A virtual run option is also available.

Explore the trails at the scenic Frances A. Crane Wildlife Management Area. Choose your challenge with 10K, 20K, or 30K looped courses. This event supports local conservation and community wellness initiatives.

A technical trail race on the Wapack Trail in Ashburnham, MA on May 9, 2026, offering 21.5, 43 and 50 mile options over rocky single track and significant elevation. Registration is limited, manually timed, and nonrefundable.

The Watuppa Trail Races offer a fast and flowy course through the scenic Watuppa Reservation. Choose from three distances: a 10K, 30K, or 50K. The event is known for its community feel and welcoming finish line.

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

The Steel Rail Races feature a marathon, half marathon, and 8K on the scenic Ashuwillticook Rail Trail in Adams, MA. Runners enjoy a technical shirt, finisher medal, and a post-race party with live music. The event supports the maintenance..

Hit the trails at Pittsfield State Park for the Tails & Trails State Forest Run. Choose from 50K, 25K, or 5-mile distances on a scenic loop course. The event supports local animal rescue organizations.

The Trav's Trail Run will take place in Newburyport on Sunday 17 May 2026. You can run 3 miles.

Run a unique 4K trail race on Cathleen Stone Island in Boston Harbor, accessed by a short ferry ride. The two-day event supports free science education for local youth and features a post-race party. Choose to run individually or with a cor..

This spring trail run on May 25, 2026, takes you through the scenic paths of Powisset Farm and Noanet Woodlands in Dover, MA. Choose from four distances, from 1.5 to 8.6 miles, in this cupless race. It's part of a farm-based series with awa..