Trail Running calendar near Medfield 2025-2026

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 the park's beautiful trails, including single tracks and steep hills, with a focus on minimizing lit..

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 set in Pisgah State Park, Chesterfield, New Hampshire. This event serves as a fundraiser for the New Hampshire Special Olympics, with all profits supporting their mission. Participants can enjoy t..

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 held at Mount Agamenticus in York, Maine, featuring a 5K and a 1-mile course. Scheduled for September 20, 2025, participants can run, hike, or stroll through the scenic trails.The event is timed using traditional stopwatches, and while there are n..

The Hooksett Kiwanis 5K Trail Race is a community-focused running event taking place in Hooksett, NH. Participants can choose between a 5K race for all runners and walkers and a Kid's Fun Run, which is a half-mile course for children aged 12 and under. The race features a scenic route that begins at..

Run for Nature is a running event organized by the Lowell Parks and Conservation Trust, taking place at Shedd Park in Lowell, MA. Participants can choose from a 5K, 10K, or a Kids 1-Mile Fun Run. The event aims to support access to nature and educational programs, with all proceeds benefiting conser..

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 5K and 10K races, along with a free 1K children's run for participants aged 10 and under. The courses showcase the n..

The Nipmuck Trail Marathon, taking place in Ashford, Connecticut, is a challenging 26.4-mile race that showcases the rugged beauty of the Nipmuck Trail. Participants can choose between the full marathon or a relay option, where two runners split the course. The race features a variety of terrains, i..

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 Midstate Massive Ultra Trail is an endurance running event taking place in New Ipswich, NH, featuring three challenging race options: 100-mile, 50-mile, and 30-mile courses. Set against the stunning backdrop of New England's autumn, the race follows the Appalachian Midstate Trail, winding throug..

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

The Ghost Train Trail Races, taking place in Brookline, 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 local conservation efforts, with all profits..

Womp Romp is an exciting running event taking place in Wompatuck State Park, Hingham, MA, featuring a 50K and a 10-mile race. Celebrating its fifth year, the event has consistently sold out, with a cap of 350 participants. The course includes a mix of single track, wide trails, and pavement, making..

The Grills Trail Run, organized by the Westerly Track & Athletic Club, is part of the WTAC Fall Race Series and features both 10-mile and 10K races. Set in the scenic Grills Preserve in Westerly, Rhode Island, the courses offer a mix of single-track and double-track trails, showcasing beautiful land..

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..

The Hamsterwheel is an exciting ultrarunning event taking place in New Boston, NH, featuring races of 6, 12, 24, and 30 hours. Celebrating its 11th year, participants will run a scenic 4-mile loop along the New Boston Rail Trail, with opportunities for both individual and team entries. Runners can e..

The TARC Stone Cat Trail Festival will take place in Ipswich on Saturday 1 November 2025. You can run between 10 and 100 kilometers.

The Tarckey Trot 6 Hour - Winchester, MA will take place in Winchester on Saturday 15 November 2025.

The Li'l Rhody Runaround Trail Run is a popular running event taking place at Burlingame State Park in Charlestown, Rhode Island. Scheduled for November 16, 2025, participants can choose between two distances: an 8-mile and a 4-mile trail run. This event is part of the WTAC Fall Race Series, offerin..