Trail Running calendar near Winchester 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 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 Bobcat Ridge 25k is a trail running event held at the Edwin L. Smith Preserve in Kennebunkport, Maine. This 25-kilometer race takes participants through scenic trails within the preserve, offering a challenging and beautiful outdoor experience.The event supports the Kennebunkport Conservation Tr..

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..

Trust Trail Fest October is a trail running event held at the Kennebunkport Conservation Trust headquarters in Kennebunkport, Maine. Participants can choose between a 5k or 10k race that winds through scenic forest trails featuring natural terrain such as rocks, roots, and possible mud. The race sta..

The Midstate Massive Ultra Trail is an endurance race held in New Ipswich, New Hampshire, featuring 100-mile, 50-mile, and 30-mile point-to-point courses that traverse the scenic mountains, fields, roads, and rivers of central Massachusetts, with border crossings into New Hampshire, Rhode Island, an..

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 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 annual ultrarunning event held in New Boston, NH, featuring races of 6, 12, 24, and 30 hours, including relay options. Runners traverse a scenic, largely flat 4-mile loop along the New Boston Rail Trail, starting near the Hillsborough County Fairground. The event encourages pa..

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. You can run between 6 and 6 hours.

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, the event features two race options: an 8-mile course and a 4-mile course, both set against the scenic backdrop of Watchaug Pond. This ra..

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k is a unique outdoor event held in Berkley, MA, designed to honor military personnel, first responders, and their K-9 companions. Participants can choose to run, ruck with weighted packs, or walk the rugged 5k trail, all while reflecting on the sacrifices..