Trail Running calendar near York Harbor 2026-2027

Run the TARC Blue Hills Skyline 12K on June 21 in Milton, MA, tackling about 2,300 feet of climbing on rocky, technical Skyline trails. Stair climbs and panoramic Boston skyline views make this a memorable trail challenge.

Take on the Summer Hill league at Ardwhallan Outdoor Pursuit Centre in West Baldwin on Sat 18 Jul 2026, a testing 4.5 km trail with 150 m of climb. Pre entry is required and junior entries welcome for a fun, competitive summer race.

Baldface Scramble in the White Mountain National Forest offers 29K and 14K routes over steep ledges and exposed ridge lines, with sections that require scrambling. Expect big climbs, mandatory safety gear and a mountain trail challenge.

Experience a packed 3.6 mile course of Nordic paths, switchback singletrack and varied footing at the Kingman Farm Trail Race. Day of event entry is available and proceeds support the Doug Flutie Jr. Foundation for Autism.

Celebrate the 10th anniversary Ragged 75 around Lake Sunapee, a three stage trail challenge of about 75 miles with 15,500 ft of climbing, or tackle the one day 50k of roughly 33 miles. Camp by the lake, race rugged trails and push your limi..

Experience the Trail Animals Running Club Summer Classic at Medfield's Noon Hill and Shattuck Reservations, a scenic and challenging 10 mile loop of forested singletrack that climbs to a Noon Hill vista. Distances include 10 miles, 40 miles..

Jigger Johnson Ultras offers rugged, technical trail races in New Hampshire's White Mountain National Forest, August 14 to 16, 2026. Choose 20, 50 or 100 mile routes that test navigation, endurance and reward big mountain views.

Firebird Trail Races on August 22, 2026 send runners on scenic single track loops through Lowell Preserve and North Falmouth Community Forest, with 13M, marathon and 50K options. Enjoy volunteer supported aid stations and a wood carved Fire..

Join the Black Bear Trail Races in Waterville Valley on Aug 29, 2026. Distances range from a rugged 50K with big climbs to a family friendly 1 mile fun run on beautiful single and double track trails.

Join the Trail Animals Fall Classic at Great Brook Farm for scenic trails and distances from youth fun runs to 50 mile ultras. Community vibe, limited spots, and on course aid make this a favorite, so bring your own hydration and register e..

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

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..

Run a point to point ultramarathon on the Midstate Trail across Massachusetts with crossings into NH, RI and CT. Choose 100 Mile, 50 Mile or 50K routes through woodlands, fields and rivers at peak fall.

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..

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.

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..

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.