Trail Running calendar near North Andover 2026-2027

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 multi day timed trail event on a Winchendon farm using a roughly two mile loop. Runners choose from six hour day or night, 12 hour, 24 hour, or 48 hour formats under the Sturgeon Moon.

A scenic off-road 5K at White Barn Farm through conservation land with a midway water station and marshaled course. Proceeds support the farm and a donation to the local food pantry.

A 4.61 mile trail race at Moody Park in Claremont NH featuring narrow single track, wet sections and a steep drop and climb at Gravity Cavity. The event is part of the Western NH Trail Running Series and benefits the local parks department.

A timed 5K at Brimfield Winery on August 15, 2026, run on a mostly grass cross country style course. Registration options include a standard 5K with a postrace wine pour and a volunteer plus run option.

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.

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.

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 5K cross-country race at Waters Farm in Sutton, MA, marking the fourth running of the Old Goat Track Club XC Classic with on-site parking, finish-line water and fruit, portable toilets, and awards for individual and team results.

Ocean State Ultra in West Greenwich, Rhode Island (August 29–30, 2026) offers a 100 mile race with a 34 hour limit plus 12 and 6 hour loop events; registration runs March 30 to August 17, 2026.

An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.

Timed loop trails on Wachusett Mountain with 7, 14, 21, and 28 mile options over ski slopes and single-track. Participants have 10 hours to finish, with weighted vest options and marked courses; finishers receive a shirt and patch.

Trail Animals Running Club hosts a multi distance trail event at Great Brook Farm State Park on September 5, 2026. Looped 10K and 10 mile courses cover distances from 10K to 50 miles, plus a youth fun run and a Yeti Mischief Mile.

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 community 5K run and walk in Nashua, NH on September 5, 2026 with free registration for veterans and children, a fee for participants 13 and older, event shirts, donation options and volunteer opportunities. Use #nashua5k for photos.

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..

A lakeside trail run in Goshen, New Hampshire on September 5, 2026, with 3 mile and 5.7 mile courses, awards, swag, and a raffle. The longer distance awards points in the Western NH Trail Running Series.

Trail races at Bear Brook State Park near Allenstown, NH offer a GPX navigated half marathon and a variable ultramarathon between 50k and 100k, with minimal course markings and cup free aid stations.

A Keene State College alumni cross-country meet on 09/12/2026 at the Keene State Athletic Complex featuring a men's 5K and a women's 2 Mile race; registration runs 09/06 to 09/12 with a $25 fee per event.