Trail Running calendar near Brookline 2026-2027

A point-to-point trail event on the New England Trail offering 112-mile and 50-mile options. Entrants must donate to the Connecticut Forest and Parks Association and provide proof; runners must self-navigate and arrange crew support.

Run a flat, out-and-back course on the scenic Holliston Rail Trail. This event offers a 5K and a 10K for adults, plus a fun run for kids with distances based on age. The community gathering point is Blair Square in Holliston.

Enjoy a 3 mile trail run through the scenic Westport Rivers Vineyard & Winery followed by a vineyard celebration with dinner, wine, and live music.

Sunapee Scramble on June 7, 2026 is an up and down mountain race at Mount Sunapee that serves as the 2026 USATF National Classic Mountain Championship and features a $30,000 prize purse. The course is about 9.2 miles with 3,250 feet of vert..

A five mile fun run along the Cheshire Rail Trail from the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.

Experience a scenic New England trail event in Dunstable with a 5 mile loop or a 6 hour timed challenge. Support the Humane Society while running through historic quarries and former ski hills.

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..

Trail races at Mansfield Hollow State Park: a ~15.7-mile out-and-back on the Nipmuck Trail and a new 5K inside the park, with proceeds supporting Connecticut trail stewardship and organized by the Shenipsit Striders.

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..

Experience a 5k obstacle mud run designed for unity and women empowerment at Kimball Farm in Haverhill. Join a supportive community for a day of teamwork and mud while supporting the National Breast Cancer Foundation.

Experience an obstacle course weekend at a lush Massachusetts farm featuring rolling hills and mud. Choose from 5k and 10k races or the kids division with onsite farm treats and a local brewery.

A multi-day loop event at Notchview in Windsor, MA featuring multiple timed and distance formats on a groomed 1.9 mile loop, on-course aid, campsite arrangements, and charitable donations to local beneficiaries.

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.

A technical 5.6 mile loop trail race in Northfield, NH where runners complete six laps within a ten hour limit, with aid stations and lap drop bags. 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.

Test your endurance at Soapstone Mountain with a five point five mile circuit featuring six mountain ascents. Run through rocky trails and finish at the mountain tower in Shenipsit State Forest.

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.

A three day trail stage race around Lake Sunapee with a 75 mile loop and a 50k option, significant elevation, overnight camp logistics, midstage aid stations, mandatory safety gear, and a limited field for the stage race.

Experience a tactical mud run in Barre Massachusetts. Choose between a 5 to 7 mile course with 25 obstacles or a 3 mile sprint featuring 15 to 20 obstacles on a technical Saturday course.