Trail Running calendar near York 2026-2027

A looped trail event at Shaw Cherry Hill Farm in Gorham, Maine on September 5, 2026, offering 50 km, 25 km, and 10 km distances on a flat, non-technical course with an aid station and volunteer support.

The Kismet Cliff Run will take place in Conway on Sunday 13 September 2026. You can run between 5 and 13 miles.

The Mt. A Trail Challenge will take place in York on Saturday 19 September 2026. You can run 5 kilometers.

A trail race in Hooksett on September 19, 2026, featuring a 5k on stone dust and wooded conservation trails and a half mile kids run for ages 12 and under. Proceeds support Hooksett Kiwanis community and youth programs.

A looped trail ultra at Wolfe's Neck Farm in Freeport with in-person 50, 30 and 10 mile options plus virtual 5, 10, 30 and 50 mile events. The course is off pavement with a single aid station at the start and finish.

Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes wit..

A point-to-point UTMB Index trail ultra on October 10-11, 2026, across central Massachusetts and nearby states, offering 100-mile, 50-mile and 50K options with significant elevation gain and wave-start seeding.

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

A multi distance trail event on October 17 and 18, 2026 in Brookline NH along the Granite Town Rail Trail, featuring a 30 hour ultramarathon and a 30 mile night race. All profits support local trail conservation.

Mountain trail race at Cranmore Mountain Resort in North Conway, NH, offering a 10K over two loops and a 5K single loop with substantial elevation gain and one aid station.

A looped trail race at Wompatuck State Park near Hingham, MA offering a 10 Miler and a 50K with mixed single track, wider trails and some paved sections. Aid stations, cupless policy, participant donations, and proceeds support charity part..

A community 5K and 10K plus a kids fun run at Emmons Preserve on October 31, 2026, organized by School Around Us. Music, on-site activities, a wood-burned finisher medal for participants and a raffle are included.

TARC Stone Cat Trail Festival in Willowdale State Forest (Ipswich, MA) offers looped trail distances from 10K to 100K, a Cider Donut Mile and a free youth fun run, with proceeds supporting local land stewardship.

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.