Trail Running calendar near Medfield 2025-2026

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 Charlie Stavros Memorial Beach Run is a free, end-of-summer 3-mile running event held at Westerly Town Beach, Rhode Island. Organized by the Westerly Track Club and the Stavros family, the race features a scenic route that includes a 1.5-mile out-and-back course along the beach at low tide. This..

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 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,..

The Bear Brook Trail Races, set in the scenic Bear Brook State Park in Allenstown, NH, offers participants a choice of three challenging races: a 10K, Half Marathon, and Marathon. The event showcases beautiful trails, including single tracks and steep hills, with a focus on minimizing litter by requ..

The Run for Nature event in Lowell, MA, is a community-focused race supporting conservation and environmental education. Held at Shedd Park, it features a 1-mile Kids Fun Run, a 5K run/walk, and a 10K trail run. The course includes trails through Shedd Park and Rogers Fort Hill Park, along with a se..

The Run for the Pumpkins Trail Run is part of the WTAC Fall Race Series, taking place at Bradford Preserve in Westerly, Rhode Island. Scheduled for October 4, 2025, the event features a 10K, a 5K, and a children's 1K run for participants aged 10 and under. The courses showcase the natural beauty of..

The Nipmuck Trail Marathon, organized by the Shenipsit Striders, is a challenging 26.4-mile trail race held in Ashford, Connecticut. The course follows a rugged segment of the Nipmuck Trail, featuring rocks, roots, mud, and wood bridges, offering a demanding experience for trail runners. Participant..

The Groton Town Forest Trail Races, organized by the Squannacook River Runners and Groton Trails Committee, feature two scenic courses of 9.5 miles and 3.4 miles through the picturesque Groton Town Forest. The trails are well-marked and consist of narrow dirt roads and winding paths, presenting a mi..

The Houghton's Pond Trail Races feature two distances: a 7-mile race and a 3.7-mile race, set in the scenic DCR Blue Hills Reservation in Milton, MA. Participants will navigate rolling dirt roads and forest paths, with elevation changes of approximately 700 feet for the 7-mile course and 300 feet fo..

The Midstate Massive Ultra Trail is a challenging endurance event held over two days in October 2025 in New Ipswich, New Hampshire. It features three race distances: 100 miles, 50 miles, and 30 miles, traversing the scenic Appalachian Midstate Trail and surrounding landscapes in Massachusetts, New H..

The Ghost Train Trail Races, taking place in New Hampshire, is a unique running event that features a 30-hour ultramarathon, relay races, and shorter distances of 15 miles and 30 miles. Established in 2009, the event serves as a fundraiser for the Brookline and Milford Conservation Commissions, with..

The Mt. Tom Trail Race is an exciting running event set against the stunning backdrop of Mt. Tom, featuring challenging terrain and breathtaking views, particularly during peak foliage.Participants can choose from a solo 25k, a 2-person 25k relay, or a solo 10k. The race supports the Kestrel Land Tr..

Tackle the Trail is a well-supported running event held in Pomfret, Connecticut, featuring multiple race distances including a marathon, half-marathon, 10K, and relay team race. The course winds through the scenic Airline Trail communities, starting in Willimantic, CT, and finishing in Putnam, CT. T..

The Weir River Farm Trail Race, scheduled for October 19, 2025, in Hingham, MA, features three race distances: 10 miles, 6.0 miles, and 3.4 miles. This annual event showcases the scenic trails of Weir River Farm and the surrounding Whitney and Thayer Woods. Participants can enjoy post-race cider don..

The Book It for Books 10K and 5K is a charity running event held at Lake Accotink in Springfield, VA. Participants can choose to run or walk, with the event supporting literacy programs and providing books to children in need. The race features a trail course around the lake, with the 5K on the sout..

The Womp Romp is an annual trail running event held in Wompatuck State Park, Hingham, MA, featuring a 50K and a 10-mile race. The event celebrates the park's natural beauty with a course that includes single track, wide trails, and some pavement, suitable for both beginners and experienced runners...

The Grills Trail Run, organized by the Westerly Track & Athletic Club, is part of the WTAC Fall Race Series and will take place at Grills Preserve in Westerly, Rhode Island. Participants can choose between a 10-mile and a 10K race, both showcasing the scenic trails and natural beauty of the area, in..

The Powisset Farm Trail Run - Fall is a part of the Barn to Run Trail Race Series, taking place at Powisset Farm in Dover, MA. This event features four race distances: 8.3 miles, 5.6 miles, 3.1 miles, and 1.5 miles, catering to both experienced and novice trail runners. Participants can enjoy post-r..