Trail Running calendar near Brookline 2026-2027

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.

Trail races in Hartford, Vermont, through the Hartford Town Forest and Conservation Area. Courses mix logging roads, packed trails, and single track, with a 5K mostly downhill and a 10K that earns Western NH series points.

A 12 hour trail event in Lawrence Woods, Medford, MA featuring an about 5 mile loop that stays in the woods, a minimal aid station, and the option for participants to set up personal support near the start area.

A one-mile out-and-back on the Farmington Canal Heritage Trail in East Granby, offered in two waves and hand timed, on crushed gravel. Limited parking and a $25 registration fee; all proceeds benefit charities.

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 stage race around Lake Sunapee covering 75 miles with ~15,500 ft gain, plus a 50k option. The format includes overnight camping, organizer gear transport, stocked aid stations, mandatory safety gear, and a $30,000 prize purse.

Experience an obstacle course with over a dozen mud pits at the 508 INTL Adventure Sports Center. Enjoy a non competitive environment featuring music, food, and a festive atmosphere for both participants and spectators.

A 12 km trail race on August 1, 2026 in Hanover, NH, using Oak Hill XC and Trescott Trails with 1,446 ft of climbing. The event offers pre-registration and race-day entry with course support and timing services.

The Anchor Down Ultra presents a series of timed ultra-marathons on the coast of Rhode Island. Runners can choose a 6, 12, or 24 hour challenge within Colt State Park.

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..

Timed trail event in Chester, Vermont on August 8, 2026 offering six and twelve hour options on a 1.8 mile loop with 280 feet of elevation per lap. Basic aid and shared food are available and the event supports local recovery and recreation..

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

Trust Trail Fest offers 5k and 10k races on forest trails at the Kennebunkport Conservation Trust headquarters, followed by music, food, a beer tent and family activities. Proceeds support the Trust in Education programs.

A community eight hour trail event of roughly 5K loops at Crandall's Park in Tolland, CT on August 15, 2026. The day includes a potluck, raffles per loop with prizes, and a 50th anniversary gift for runners who complete at least one loop.

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.

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.

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.

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.