Trail Running calendar near Boston 2025-2026

The North Kingstown Firefighters Association Blazing Trail 5K is a first-year fall trail run/walk held at Ryan Park in North Kingstown, Rhode Island. The 5K course follows a scenic park trail, welcoming runners and walkers of all ages and experience levels. Proceeds benefit the North Kingstown Firef..

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 take place in the scenic DCR Blue Hills Reservation in Milton, Massachusetts, just south of Boston. This event offers two trail race distances: 7 miles and 3.7 miles, both starting and finishing near the Houghton's Pond Visitor Center. The courses feature rolling terr..

NipMuck Trail Marathon, in Ashford, CT, features two options: the original NipMuck Trail Marathon (26.4 miles) and a two-person NipMuck Relay. The race uses a 13-mile middle segment of the Nipmuck Trail, running south to Route 44, back to the start, then north to Boston Hollow before finishing at Pe..

Trust Trail Fest October 2025, hosted by the Kennebunkport Conservation Trust, offers a 5k and a 10k trail challenge. Runners and walkers navigate the Trust’s forest trail system, finishing at the headquarters at 57 Gravelly Brook Road in Kennebunkport, ME. The course features rough terrain—rocks, r..

The Groton Town Forest Trail Races, held in Groton, Massachusetts, offer two challenging trail running distances: 9.5 miles and 3.4 miles. The courses wind through the scenic Groton Town Forest, featuring well-marked paths with no road crossings, combining narrow dirt roads and single-lane trails fi..

Keene Family YMCA Fall Foliage Trail Races in Keene, New Hampshire offer 5K and 10K trail runs starting and finishing at the Keene YMCA (200 Summit Road). The 5K provides a fast, beginner-friendly taste of trail running, while the 10K adds more challenging rolling singletrack and elevation. Runners..

Stairs4RTroops 2025 at Gillette Stadium in Foxboro, Massachusetts is a stair climb, walk, or run up the stadium stairs and around the lower concourses. Held on October 5, 2025, the event features multiple waves roughly every 15 to 30 minutes, including a special Firefighter Wave. The first 2,000 reg..

Midstate Massive Ultra Trail is a UTMB Index endurance race held October 11–12, 2025, spanning New Ipswich, NH, and central Massachusetts with border crossings into New Hampshire and Rhode Island. Runners choose from three point-to-point options—100 miles, 50 miles, and 50 kilometers—following the A..

The Wayland / HFC Striders XC Festival, held in Wayland, Massachusetts, is a vibrant cross-country running event featuring three youth 3K races and two open 5K races for adults. The course winds through scenic fields and wooded trails, offering a challenging and enjoyable experience for runners of a..

Vulcan's Fury Trail Race in Nottingham, New Hampshire offers two rugged courses—the Half Marathon and the 5 Miler—set on hiking trails through a once volcanic landscape at Pawtuck. The course is described as technical and scenic, featuring a massive boulder field, dense forest, single-track switchba..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 42 kilometers.

The Ghost Train Trail Races, held in Brookline, New Hampshire, are a series of trail running events along the historic Granite Town Rail Trail. This mostly flat, well-groomed course follows an old railroad bed used in the late 19th and early 20th centuries, featuring a mix of dirt and about one mile..

United We Move Trailfest, held annually in Fall River, MA, takes place in the scenic Fall River Bioreserve. Participants can choose to walk, run, or ride on various courses: a 1.1-mile Tattapanum Trail or 5K walk; 5K or 10-mile runs on mixed terrain including paved, dirt, and grassy trails; and 10 o..

Located on Mansfield's WWII Veterans Memorial Trail in Massachusetts, the WWII Veterans Memorial Trail Weighted Race is a 2.5-mile out-and-back loop on a rail trail with paved, gravel, and grass sections. In this 6-hour timed event, participants carry weight per lap, with their lap distance multipli..

The Weir River Farm Trail Race, held annually in Hingham, Massachusetts, offers runners three trail distances: 10 miles, 6 miles, and 3.4 miles. The race courses wind through the scenic trails of Weir River Farm, Whitney, and Thayer Woods, with the 10-mile route including additional loops in Wompatu..

The Ravenswood Trail Race will take place in Gloucester on Sunday 19 October 2025. You can run between 4 and 4 miles.

Womp Romp Trail Race is held in Hingham, Massachusetts at Wompatuck State Park (South Field). It offers a 50K (three loops plus a mile) and a single-loop 10-mile option. The course blends single-track, wide trails, and some pavement, with about two miles of pavement per loop.It’s a cupless race, so..

Pumpkin Pacer 5k @ White Barn Farm is a 5K off-road trail run/walk held at White Barn Farm, 431 South Street, Wrentham, MA 02093. It’s the final race in the Farm To Trail 5K Series and is open to all ages and abilities. The course weaves through scenic conservation land and farm property, featuring..

Powisset Farm Trail Run - Fall is a Barn to Run Trail Race Series event held at Powisset Farm in Dover, MA, on October 26, 2025. The course spans Powisset Farm and adjacent Noanet Woodlands, with four distance choices: 8.3, 5.6, 3.1, and 1.5 miles. The atmosphere blends competitive trail running wit..