Trail Running calendar near Boston 2026-2027

Enjoy a scenic 3 mile trail at Sakonnet Vineyard, then celebrate with wine, dinner, music and a souvenir wine glass. BBQ only and kids BBQ options are available for those who prefer to skip the run.

Join a scenic trail run through NE Connecticut along the Air Line State Park Trail with marathon, half, 10K, relay and junior distances. Tackle the Trail supports local students pursuing higher education.

Run the Ghost Train Trail in Brookline, New Hampshire amid peak fall foliage. Choose ultramarathon, relays, haunted 30 mile night or 15 mile race and help fund local conservation and trail preservation.

Join the Womp Romp at Wompatuck State Park for muddy, scenic trail loops through South Field with 10 Miler and 50K options and hearty aid stations. Proceeds support local charities for a fun, community focused fall run.

Celebrate community and fitness at the Holistic Hustle 5K and 10K at Emmons Preserve in Kennebunkport. Family friendly fun with music, treats, face painting and a wood burned finisher medal while supporting School Around Us.

TARC Stone Cat Trail Festival at Willowdale State Forest in Ipswich, MA offers distances from a cider donut mile and youth run to serious ultras up to 100K. Rugged 12.5 mile loops of roots, rocks and rolling terrain make for a scenic, chall..

Enjoy scenic trails around Watchaug Pond at the Li'l Rhody Runaround on November 15, 2026, with 8 mile and 4 mile course options. Part of the WTAC Fall Trail Race Series, it welcomes runners of all levels.

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.