Trail Running calendar near Winchester 2025-2026

The Trav's Trail Run will take place in Newburyport on Sunday 18 May 2025. You can run between 3 and 3 miles.

The Soapstone Mountain Trail Races, taking place on May 18, 2025, in Stafford Springs, CT, features two scenic races: a 25K and a 6K "Sampler." Both courses wind through the picturesque Soapstone Mountain area and Shenipsit Forest State Park. The event emphasizes community and environmental stewards..

The 4K Trail Run is a unique running event taking place in Boston, Massachusetts, on May 21 and 22, 2025. Participants can register as individuals or as part of corporate teams, making it a versatile option for runners of all backgrounds. The event not only promotes physical fitness but also support..

Ocean State Ultra is an exciting running event taking place at Big River State Management Area in West Greenwich, Rhode Island. Scheduled for May 24, 2025, the event features three race categories: a challenging 100-mile race, a 12-hour endurance challenge, and a 6-hour race. Participants can expect..

The Manchester 2 Monadnock Ultramarathon is a challenging 55-mile race set in the scenic landscapes of southern New Hampshire, taking place on May 24, 2025. This point-to-point event features a mix of terrain, including roads, dirt paths, and trails, with a total elevation gain of over 6000 feet. Ru..

The Taunton Trail Half Marathon is an exciting running event designed for both beginners and experienced trail runners. Set in the picturesque surroundings of Taunton's waterways, the course is ultra-flat and fast, making it ideal for those looking to achieve personal bests. Participants can enjoy t..

The Powisset Farm Trail Run - Spring is a part of the Barn to Run Trail Race Series, taking place on Memorial Day, May 26, 2025, 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 novice and experienced trail runne..

The Sunapee Scramble is a challenging mountain running event taking place in Sunapee, New Hampshire, on June 1, 2025. This race will serve as the USATF National Classic Mountain Championship and the sole selection race for the 2025 US Classic Up/Down Mountain Running Team, which will compete in Spai..

The Drummer Hill Trail Races, taking place in Keene, NH, offers a variety of race distances including 50K, 37.5K, 25K, and 12.5K. Participants can choose how many 12.5K laps to complete, allowing for a flexible and personalized racing experience. The course features technical terrain with elevation..

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 of approximately 3 miles through the vineyard, culminating in a festive atmosphere with dinner, wine, and live music. The event is designed for ind..

The Nipmuck South Trail Race is a scenic 15.7-mile out-and-back race held in Mansfield, Connecticut, primarily along the beautiful Fenton River. Participants will encounter diverse terrain, including small bridge crossings and a climb to a 50-foot cliff. The event features three water stops and supp..

The Spaulding Woods 50K is a challenging trail race set in Northfield, NH, featuring a technical 5.6-mile loop that includes rocks, roots, and footbridges. Runners have ten hours to complete six laps, totaling approximately 34 miles with a significant elevation gain of 4,400 feet. The event supports..

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 Anchor Down Ultra is a prestigious ultra-marathon event held at Colt State Park in Bristol, Rhode Island. It features three race durations: 6-hour, 12-hour, and 24-hour, catering to various levels of endurance runners. Recognized as one of the "Best Races in America" by Men's Health Magazine, th..

The Tarc Summer Classic will take place in Medfield on Saturday 16 August 2025.

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

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 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..