Trail Running calendar near Melrose 2026-2027

A 4.9 mile mountain trail race in Keene, NH on October 25, featuring four up and down laps on different trails, 1650 feet of elevation, prize money and age group awards, with proceeds supporting the Keene Community Kitchen.

A fall trail 5k in Berkley MA combining running, rucking, and walking to honor military, first responders, and K9s. Dogs are allowed on leash with a waiver and proceeds support local canine and service organizations.

A fall trail run at Powisset Farm in Dover, MA with four distances on meadow and woodland trails, a cupless aid station, post race cider donuts and family activities including a barnyard and pumpkin painting.

A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.

A stadium stair-climb at Gillette Stadium where participants run, walk, or roll through about 5,184 steps in support of Homes For Our Troops. The event offers team and wheelchair waves, optional fundraising, and spectator registration.

A fourth annual community run at Emmons Preserve in Kennebunkport offering timed 5K and 10K races plus a kids 1/2 mile fun run, music, family activities, a wood burned finisher medal and a raffle with local prizes.

A costumed 5K trail run on October 31 2026 at Wells Reserve at Laudholm. Timed course with water stations and awards, with proceeds supporting coastal conservation and restoration.

Hugs From Vets Trail 10Kish in Henniker, New Hampshire on November 1 features a mixed trail and country road course and raises funds for American Legion Post 78. The field is limited to 150 participants and awards are given to overall and a..

A stadium obstacle race weekend at Fenway Park on November 7-8, 2026 featuring a 5 km Stadion with 20 obstacles, a kids race, and spectator access inside and around the historic ballpark.

A multi-duration timed trail event in New Boston, NH on a 4.0 mile marked loop along the Piscataquog River. Options include solo and relay times, chipped bib timing, central aid station services, team entries, and 100 mile buckles.

A November trail festival at Willowdale State Forest in Ipswich offering multiple looped distances from a 10K to 100K, a Cider Donut Mile, and a flagged 0.5‑mile youth run, with cupless aid stations and fundraising for local land trusts.

A last runner standing backyard ultra on private farmland in Winchendon with a 4.1666 mile loop. The event also offers 6 hour, 12 hour and 24 hour timed options plus a standalone fastest lap competition.

A looped 3.1-mile trail course at White Barn Farm in Wrentham MA with distances from 5K to 50K and a central aid station. Runners complete repeatable laps and may stop after any finished loop.

Trail races in Upton State Forest offer 10.5K and half marathon options over technical, hilly single track and forest roads. The event has a 250 runner cap and aid stations spaced roughly every three miles.

A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.

A 6 hour timed trail race on a 5K loop at Wright Locke Farm in Winchester Massachusetts, featuring rocky rolling singletrack, a barn aid station in a cupless format, and provisions for adaptive athletes and youth discounts.

Windham Woods School holds its 3rd annual Thankful Trails 5K on November 14, 2026 with a two loop 3.1 mile trail course, a free Kids Fun Run for ages 8 and under, an event raffle, and a limited field of 200 participants.

A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

A trail running event at Middlesex Fells Reservation with **8 mile**, **32 mile**, and **40 mile** loop options on the white blazed Skyline Trail. The course is technical and minimally marked, cupless with two aid stations and specific cour..