Trail Running Calendar Massachusetts 2026-2027

Experience a festive trail race in Salisbury this Easter weekend. Choose between timed 5K and 10K trail runs or a vibrant 1 mile color run that supports local parks and recreation.

Experience a USATF sanctioned 10 mile out and back trail run along the Merrimack River. Enjoy a community atmosphere with unique homemade prizes and support local trail maintenance efforts in Andover.

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.

Test your endurance on a scenic five kilometer trail loop in Wrentham Massachusetts. This supported race offers forty and fifty mile challenges with a twelve hour cutoff and consistent access to aid stations.

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.

Experience a scenic 5k trail run through conservation land and working farmland in Wrentham. Celebrate Earth Day with an off road course featuring natural obstacles and community focused agriculture support.

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.

Experience a trail run or walk through the campus of The Hartsbrook School in Hadley. Choose between a 5k or a 1 mile race on natural terrain while supporting local land stewardship and agricultural education programs.

Experience an all trail race through the scenic Frances A. Crane Wildlife Management Area. Choose between 10K, 20K, or 30K distances on a repeating loop course in East Falmouth.

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.

Trail races at Watuppa Reservation in Fall River on May 9, 2026, featuring grassy fire lanes, winding single track and aid stations each lap. Distances offered are 10K, 30K and 50K.

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.

Experience the beauty of the Ashuwillticook Rail Trail with a marathon, half marathon, or 8K race. This annual event includes USATF certified courses, finisher medals, and a dedicated kids run for families.

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.

Run or walk a 5k on the Southern New England Trunkline Trail in Franklin. This event supports the development of an abandoned rail bed into a multi use path connecting local communities.

Celebrate the eighth annual Trillium Spring 5K in Canton or participate virtually from anywhere. Join over 500 runners at the brewery to support Girls on the Run Greater Boston with races for adults and children.

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

Experience a unique trail race on Cathleen Stone Island in the Boston Harbor. Enjoy a scenic ferry ride and a chip timed run followed by dinner and drinks to support science education for Boston youth.