Trail Running calendar near Freeport 2026-2027

Two trail race options in Chatham, NH that cross the Baldfaces and include exposed ledges and steep climbs. Runners must carry mandatory mountain gear and meet experience qualifications.

A roughly 3.8 mile trail race at Kingman Farm in Madbury, NH on July 26, 2026, featuring rolling nordic style paths and switchback singletrack; proceeds support the Doug Flutie Jr. Foundation for Autism and day of registration is available.

Scribners Mill 5k is a trail race in Harrison, Maine that follows woods and river views through the Crooked River Forest. Part of the Loon Echo Race Series, proceeds support Loon Echo Land Trust.

The event is cancelled. It had been planned as a 10K ruck obstacle course at Pineland Farms in New Gloucester, Maine, featuring The Crucible with 20+ obstacles and prize rules requiring participants to ruck the full course with a pack.

KCT Trail Fest 2026 in Kennebunkport, ME offers a 5k walk or run and a 10k run on August 9, 2026, with courses on local trails and a finish-area gathering that includes music, a beer tent, food and family games.

A rugged trail race at Bradbury Mountain State Park in Pownal, Maine, featuring a twisting 12 mile single-track loop with rocks, roots and hills. The event is the third race in a capped series organized by a nonprofit volunteer group.

A multi distance trail event in the White Mountain National Forest near Waterville Valley, New Hampshire held August 14 to 16, 2026. Races include 100 mile, 50 mile and 20 mile routes with substantial elevation gain and mandatory mountain g..

A scenic trail 5K on Wanakee’s 227 acre site in the White Mountains and Lakes Region of New Hampshire, held during Wanakee Homecoming. Proceeds support a camp scholarship fund and facility improvements.

Trail races in Windham, ME on technical single-track loops with 13M, marathon, and 50K options; two aid stations, on-course markings, wood carved finisher medals, and a required participant donation to local trail nonprofits.

Join the PRHS XC Alumni Race in Minot for a 5K trail run and kids fun run. This community event features friendly competition between alumni and current students followed by a barbecue and kickball.

A trail race weekend in Waterville Valley, New Hampshire, offering *50K*, *23K*, a 4 mile trail, and a 1 mile Bear Cub Fun Run; the 50K includes 7,700 feet of climbing and requires specific mandatory gear.

Two trail races at Five Fields Farm in Bridgton, ME: the Bald Pate 10k through pitch pine forest and the Five Fields 50k on a figure-8 course through Bald Pate and Holt Pond preserves. Proceeds benefit Loon Echo Land Trust.

A weekly fall trail running and walking series at Great Glen Trails in Gorham, NH from Sep 3 to Oct 8, 2026. Choose from 5 km, 3 km or 1.5 km courses; dogs on leash are welcome and one-time entries are available on-site.

Test your endurance at Pineland Farms in Maine with this backyard ultra trail race. Run a 4.2 mile loop through pristine wooded trails and see how many laps you can complete in this last person standing format.

Experience a flat and non technical trail race at Cherry Hill Farm in Gorham Maine. Choose between 50k 25k or 10k distances consisting of multiple loops around the scenic farm property.

A trail running weekend around Mirror Lake in West Newfield, Maine, with laps of about 3.6 to 3.8 miles through forest roads and singletrack. The weekend includes a Saturday gravel ride, onsite camping, youth runs, and a post ride gathering..

Three trail races in Camden Hills State Park present 10K, 20K and 50K courses around Mount Megunticook, with routes ranging from steep singletrack to wide gravel trail and an Indigenous land acknowledgement and giving option.

A September mountain trail event at Echo Lake State Park offering a technical 5-mile Little Beast and a rugged 13.1-mile Beast of the East with big climbs, granite ridge sections, and limited on-course support.

Big Brad Ultras at Bradbury Mountain State Park offers 25K and 50K options on a 15.5 mile single track loop. The course features technical terrain, multiple aid stations, drop bag access, and significant elevation gain.

The 12th Annual Skyline Farm 5K Trail Run & Walk on September 13, 2026 offers a scenic course through fields, hills and woods, a free Kids' 1K with prizes, post-event food and music, and awards including gift certificates and pies.