Trail Running calendar near Derry 2026-2027

Explore the hill towns of western Massachusetts on a mix of trails and dirt roads. Choose from a 50k, 30k, or 10k distance, with all proceeds supporting the Franklin Land Trust's conservation efforts at the scenic Edge Hill Conservation Are..

Run a scenic yet rugged half marathon trail race at Lynn Woods Reservation in Massachusetts. This 13.1-mile event features three challenging loops showcasing the historic Stone Tower. The focus is on sustainability and a centralized start/f..

UltraTrax Cranmore is a summer endurance walk in the White Mountains featuring 7 to 28 mile options on a scenic 1,775 foot elevation loop. Participants can walk, hike, or ruck with added weight to earn finisher patches and medals.

Enjoy a community celebration in Portland with a 10k trail race, scenic bike rides, or a family friendly 2 mile walk. Finish the day with a festival featuring food trucks, music, and local beer to support Maine trails.

Kick off Tamworth Family Day with this scenic 5k on July 4th. The point-to-point course tours the village and trails, finishing with ice cream and a bib raffle. It's a local tradition celebrating community arts and culture.

Gather your team for a two day relay through the scenic Vermont countryside. Run flowy single track trails and camp under the stars at the Ascutney Outdoor Center for an unforgettable weekend of adventure.

The Spaulding Woods 50K is a technical trail race on a 5.6-mile loop in Northfield, New Hampshire. Runners complete six laps, with 4,400 feet of elevation gain, within a ten-hour limit. The event supports Spaulding Academy & Family Services..

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.

Join a community trail run or walk at Owen Bell Park to support the Ryan French Memorial Scholarship Fund. This family friendly event features a 5K trail, a walk, and a free kids fun run.

The Kingman Farm Trail Race is an old-school, show up and race event over 3.8 miles of rolling nordic paths and switchback singletrack. It benefits the Doug Flutie, Jr. Foundation for Autism. Day-of registration is available.

The Ragged 75 offers a rugged three-day stage race and a demanding 50k on the scenic SRKG Greenway trails in New Hampshire. Runners summit multiple peaks over technical terrain, with overnight camping and a communal atmosphere. The event ma..

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..

Lover's Lane is a timed trail run on a 1.8-mile loop in Chester, VT. Participants can choose 6-hour or 12-hour options in a community-supported, fat-ass format. The event supports local recreation and recovery services.

The 5K Race to the Ledges will take place in Concord on Saturday 8 August 2026. You can run 5 kilometers.

Test your endurance in the White Mountains of New Hampshire with distances ranging from 20 to 100 miles. Navigate technical trails and significant elevation gains in this rugged mountain event starting from Waterville Valley.

Experience a scenic off-road trail run or walk through the conservation lands of White Barn Farm. This cup-less 5k event supports local sustainable agriculture and community food security in Wrentham.

The Firebird Trail Races in Windham, Maine offer rugged trail running on a technical loop through the Lowell Preserve. Choose from a 13-mile, marathon, or 50K distance on a course marked by rocks and roots. This grassroots event supports lo..

The annual Vineyard Hill Trail Run features a scenic 5K/10K course over Vineyard Hill and through Bradley Palmer State Park. It's part of the North Shore Trail Series and includes a fully marked trail with an aid station.

Experience a classic 5k cross country race through the scenic fields of Waters Farm in Sutton. Join the USATF New England Grand Prix season opener on a spike friendly course with both open and masters divisions.

Join the Black Bear Trail Races in New Hampshire's scenic Waterville Valley. Choose from four trail distances, including a 50K with major mountain climbs. All runners receive a finisher's medal and finish near the Town Square.