Trail Running calendar near Portland 2026-2027

A roughly six-mile uphill trail race to Loon Mountain’s North Peak with about 3,066 ft of climb, very steep sections including the one-kilometer Upper Walking Boss, two fluid stations, and over $20,000 in prize money.

A two lap, 9 mile trail race on Bradbury Mountain State Park featuring hilly technical single track and a three hour cutoff. The field is limited to 160 runners and the event is part of the Bradbury Mountain Trail Race Series.

Tough Mountain Challenge is a 5K obstacle-course event at Sunday River Resort on July 25, 2026, with multiple waves over the day. The course runs on ski trails and wooded terrain and includes custom-built obstacles and muddy sections.

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.

A 5 km trail race at Scribner's Mill on the Crooked River in Harrison, Maine. Pine-lined singletrack and river views, with proceeds supporting 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.

The 15th Annual 5k Race to the Ledges in Concord, NH on August 8, 2026 features a short road and trail course and includes post-race brunch boxes to take away. Registration includes an adult 5 km entry and a free kids 5 km for ages 6 and un..

A community 5K on August 8, 2026 at Pinkerton Academy in Derry, NH featuring a campus-and-trail course; runners and walkers of all ages are welcome and proceeds support the Pinkerton Fund to benefit students.

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.

Experience a scenic trail run through Vineyard Hill Reservation and Bradley Palmer State Park. Choose between 5 km and 10 km distances on a rolling course featuring wide trails and the open landscapes of Shaw Field.

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 ultramarathon at Prospect Acres Ranch where runners complete repeated 2.2 mile laps in 2, 4, or 8 hour formats. Field camping is available Friday evening and registration is $40 with proceeds supporting future events.

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.

Trail races at Five Fields Farm in Bridgton ME include a three lap 50K figure 8 and a steep, technical 10K, both starting and finishing at an apple orchard with multiple aid stations and course maps provided.

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.