Trail Running calendar near Medford 2025-2026

The Bear Brook Trail Races, held in Allenstown, New Hampshire, showcase the scenic beauty of Bear Brook State Park with its diverse trails, including single track paths, steep hills, and blueberry fields. The event offers three race distances: a 10K following "Mindy's Loop," a Half Marathon, and a M..

Run for Nature in Lowell, MA, is a community-focused running event held at Shedd Park, featuring a 10K trail run, a 5K run/walk, and a 1-mile Kids Fun Run/Walk. The course winds through scenic trails in Shedd Park and Rogers Fort Hill Park, including a stretch along the Concord River Greenway, with..

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 Aggie Ram Trail Run 5k will take place in Walpole on Sunday 5 October 2025. You can run between 5 and 5 kilometers.

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 NipMuck Trail Marathon, held in Ashford, Connecticut, is a challenging 26.4-mile trail race along the scenic Nipmuck Trail. The course features diverse terrain including rocks, roots, mud, and wood bridges, with a route that heads south 6.2 miles to Route 44 and back, then north 7 miles to Bosto..

Trust Trail Fest, held at the Kennebunkport Conservation Trust headquarters in Kennebunkport, Maine, offers participants a choice between a 5k walk/run and a 10k run through scenic forest trails. The courses feature natural terrain with rocks, roots, and occasional mud, providing a challenging and 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 a challenging point-to-point endurance race held in New Ipswich, New Hampshire, traversing the Appalachian Midstate Trail through central Massachusetts and crossing into New Hampshire, Rhode Island, and Connecticut. Scheduled for October 11-12, 2025, it offers thr..

The Ghost Train Trail Races, held in Brookline, New Hampshire, is the state's original 30-hour ultramarathon event along the historic Granite Town Rail Trail. Participants can choose from multiple race options including a 30-hour ultramarathon, a 30-hour 7-person relay, a 30-mile haunted night race,..

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..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 26 miles.

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 is a charitable running event held at Lake Accotink Park in Springfield, Virginia. The race features a 10k course that combines mostly trail running with some paved sections, including out-and-back routes on both the north and south sides of the lake. It benefits Reading is..

Womp Romp is an annual trail running event held in Wompatuck State Park, Hingham, Massachusetts, featuring a 10-mile single loop and a 50K race consisting of three loops plus an additional mile. The course offers a mix of single track, wide trails, and some paved sections, suitable for both novice a..

The Powisset Farm Trail Run - Fall is a popular trail running event held at Powisset Farm in Dover, Massachusetts. Scheduled for October 26, 2025, it offers four race distances: 8.3, 5.6, 3.1, and 1.5 miles, traversing scenic trails through Powisset Farm and the neighboring Noanet Woodlands. The rac..

The Hamsterwheel in New Boston, NH, is a unique ultrarunning event featuring 6, 12, 24, and 30-hour races, including relay options. The course is a scenic, largely flat 4-mile loop starting near the Hillsborough County Fairground, running along the New Boston Rail Trail by the Piscataquog River to L..

The TARC Stone Cat Trail Festival is a renowned trail running event held annually in Ipswich, Massachusetts, within Willowdale State Forest. Offering a variety of distances including 10K, half marathon, marathon, 50-mile, and 100K races, plus a free youth fun run, the festival features a challenging..

The TARCkey Trot is a unique 6-hour timed running event set on a scenic 5K loop at Wright Locke Farm in Winchester, MA. Participants can run as many loops as they wish within the time limit, navigating a course filled with natural terrain challenges. The event promotes community engagement, offering..

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..