Trail Running calendar near Winchester 2025-2026

The Wine Run at Sakonnet Vineyard is a unique running event scheduled for June 7, 2025, in Little Compton, RI. Participants can enjoy a scenic trail run through the vineyard, culminating in a festive atmosphere with dinner, wine, and live music. The course spans approximately 3 miles and features va..

The Nipmuck South Trail Race is a 15.7-mile out-and-back trail run held at Mansfield Hollow State Park in Mansfield, Connecticut. The scenic course follows the Fenton River and features varied terrain including small bridge crossings, a climb to a 50-foot cliff, fields, and woods. Runners encounter..

The TARC Blue Hills Skyline Trail Run is a challenging 12K race set in the scenic Blue Hills Reservation in Milton, Massachusetts. Participants will tackle approximately 2,300 feet of elevation gain on a rugged course featuring rocky terrain, steep climbs, and technical descents, all while enjoying..

The Last Human Standing event in West Greenwich, RI, is an endurance race held on private property near the Big River Management Area. Participants race on a loop, with each lap starting every hour and requiring completion within 60 minutes. Racers continue to run successive laps until only one rema..

The Flat Rock Trail Race is a new trail running event held in Dunstable, Massachusetts, benefiting the Humane Society for Greater Nashua's building expansion. Participants can run a 5-mile loop with nearly 600 feet of elevation gain, starting at the Arched Bridge and passing through scenic areas suc..

The Spaulding Woods 50K is a challenging trail race held in Northfield, New Hampshire, featuring a 5.6-mile technical loop with rocks, roots, and footbridges. Runners complete six laps over approximately 34 miles within a 10-hour time limit, with 4,400 feet of elevation gain. The course is primarily..

Ocean State Ultra is an exciting running event taking place at Big River State Management Area in West Greenwich, Rhode Island. Scheduled for July 26, 2025, the event features three race categories: a challenging 100-mile race, a 12-hour race, and a 6-hour race. Participants can expect a mix of terr..

The Soapstone Assault is a challenging approximately 5-mile trail race held at Soapstone Mountain, featuring a unique course that requires participants to climb the mountain six times. This event is designed for those seeking a rigorous hill workout, as runners navigate steep, rocky, and potentially..

The Kingman Farm Trail Race will take place in Madbury on Sunday 27 July 2025. You can run 3 miles.

The Anchor Down Ultra is a premier ultra-marathon event held at Colt State Park in Bristol, Rhode Island. This seaside race features three distinct events: a 6-hour, a 12-hour, and a 24-hour ultra-marathon, catering to various levels of endurance runners. Recognized as one of the "Best Races in Amer..

The GTA Challenge will take place in Greenfield on Saturday 16 August 2025.

The Tarc Summer Classic will take place in Medfield on Saturday 16 August 2025. You can run between 10 and 40 miles.

The Greenbelt's Vineyard Hill Trail Run is an annual event held on August 23, 2025, in South Hamilton, Massachusetts. Part of the North Shore Trail Series, it features 5K and 10K trail races through scenic areas including Vineyard Hill, Bradley Palmer State Park, and along the Bay Circuit Trail. The..

The TARC Fall Classic will take place in Carlisle on Saturday 6 September 2025. You can run between 10 and 50 miles.

The Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Sunday 14 September 2025. You can run between 5 and 5 kilometers.

The Wine Run at Westport Rivers Vineyard & Winery is a scenic running event scheduled for September 14, 2025, in Westport, MA. Participants can enjoy a beautiful trail run through the vineyard, covering approximately 3 miles amidst picturesque farms and vines. After the race, attendees can indulge i..

The Pisgah Mountain Trail Races, organized by the Red Clover Rovers, feature a 50K and a 23K trail race in Pisgah State Park, Chesterfield, New Hampshire. Scheduled for September 14, 2025, this event serves as a fundraiser for the New Hampshire Special Olympics, with all profits supporting their mis..

The Mt. A Trail Challenge is an annual running event taking place at Mount Agamenticus in York, Maine. Scheduled for September 20, 2025, the event features two courses: a 5K and a 1-mile challenge, allowing participants to run, hike, or stroll.The race is timed traditionally with stopwatches, and wh..

The 2025 ACT Trail Fest, held at 257 Limerick Road in Arundel, Maine, offers a scenic trail running experience through the Arundel Conservation Trust's multi-purpose trails and the Eastern Trail. Participants can choose from a 5K, 10K, or half marathon, all starting and finishing at the Arundel Muni..

The Hooksett Kiwanis 5K Trail Race is an exciting running event taking place in Hooksett, NH, featuring a 5K race for all runners and walkers, as well as a Kid's Fun Run for children aged 12 and under. The race begins at Heads Pond trail and follows a scenic route through wooded conservation areas,..