Trail Running calendar near Holliston 2026-2027

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.

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.

The Soapstone Assault will take place in Somers on Sunday 26 July 2026. You can run 6 miles.

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.

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.

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

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..

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

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 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.

Ocean State Ultra is a loop trail event at Big River Management Area in West Greenwich, Rhode Island offering 100 mile, 12 hour and 6 hour races. The course uses 10 mile loops with trails, short pavement sections, and staffed aid stations.

Traverse the scenic ski slopes and forest trails of Wachusett Mountain in this timed event featuring loops from 7 to 28 miles. Earn a finisher medal within 10 hours and enjoy a post trek party at the mountain base.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

Join the Trail Animals Fall Classic at Great Brook Farm for scenic trails and distances from youth fun runs to 50 mile ultras. Community vibe, limited spots, and on course aid make this a favorite, so bring your own hydration and register e..