Trail Running calendar near Drakes Island Beach 2026-2027

A two day obstacle event at Fenway Park in Boston featuring a Stadion 5K with 20 obstacles, a kids race, and spectator access. The course uses stadium features including the Green Monster, clubhouse, and home plate.

Timed running event offering several durations in New Boston, NH on a 4.0 mile loop along the New Boston Rail Trail. Chip timing, a central aid station, 100 mile buckles for individuals and teams, and specific pacer and camping rules apply.

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 night mountain race at Cranmore Resort on November 7, 2026 offering 5k and 10k courses across ski trails and access roads. Headlamps are required and the event includes bib swag, pizza, apres, and awards.

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.

A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.

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 Thanksgiving morning trail 5k in Jackson, New Hampshire, with a 1 km kids fun run for ages 10 and under. Proceeds benefit Jackson Grammar School and Girls on the Run.

A trail running event at Middlesex Fells Reservation with **8 mile**, **32 mile**, and **40 mile** loop options on the white blazed Skyline Trail. The course is technical and minimally marked, cupless with two aid stations and specific cour..

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 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 and a 1 mile Color Run in Salisbury on March 27, 2027, featuring 10K, 5K and a non timed color run, with proceeds supporting Salisbury Parks and Recreation.

The TARC Spring Classic takes place April 24, 2027 in Jericho Town Forest, Weston, MA, with 10K, half marathon, marathon and 50K looped trail options, a single aid station, marked course, and a cupless race format.