Trail Running calendar near Brewster 2025-2026

The Travis Fuller Invitational takes place in Buzzards Bay, Massachusetts, at Buzzards Bay Park, on Saturday, September 20, 2025, as part of Massachusetts Maritime Homecoming Weekend. The event offers three races: Women’s 5K, Men’s 8K, and Team Travis 5K. The site highlights a homecoming, community-..

Codfish Bowl is the 57th annual cross-country meet held at Franklin Park, Boston, MA, and is part of the USATF New England XC Grand Prix. The event features a women's 5K and a men's 8K on modified courses (3 laps for the 5K, 4 laps for the 8K) because traditional courses are unavailable due to stadi..

The BLS Wolfpack 5K Cross Country Run or Walk is a 5K event in Boston’s Franklin Park, using the historic Franklin Park cross-country course. It brings together the Boston Latin School community—students, staff, families and alumni—for a morning of running or walking, with the pep band adding energy..

The Survival of the F.I.T.test - 30+ Hour Trail Ultra is a challenging endurance event held in Cumberland, Rhode Island. Participants can choose between two course options: a flat, fast 2.1-mile loop or a more rugged 4.2-mile trail loop used in previous years. The event offers multiple race formats..

Homecoming Chargers 5k Run/Walk is a community event in Blackstone, Massachusetts, scheduled for Saturday, September 27, 2025, at 175 Lincoln Street. The 5k Run/Walk uses Blackstone-Millville Regional's home cross-country course, offering a mix of grass and pavement with a finish on the track. The e..

Ocean State XC Invitational features the Ocean State 5K Trail Run, held at Goddard Park in Warwick, Rhode Island (1095 Ives Road). The 5K course winds through bay-side trails and grasslands, described as a fast, flat off-road route with the start and finish near the clubhouse for the public golf cou..

Sheriff's Meadow Foundation hosts its Third Annual Trail Run on Martha's Vineyard, Edgartown, at the Caroline Tuthill Preserve. The course features a 3.2-mile loop through a diverse landscape of oak and pitch pine forest, salt marsh, and open meadow, starting from a field along Edgartown-Vineyard Ha..

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 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..

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..

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..

ORR Alumni Trail Race is a 5k run/walk held in Marion, Massachusetts, on the Washburn Park cross-country course. The event invites supporters to back the Old Rochester Regional cross country and track and field teams, with all proceeds directed toward uniforms and equipment. Participants traverse we..

United We Move is an annual trail event held in Fall River, MA, set within the scenic Fall River Bioreserve. Participants can choose from multiple distances and activities, including a 20-mile and 10-mile gravel bike ride, 10-mile and 5K runs, and 5K and 2-mile walks. The courses feature a mix of tr..

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, part of the North Shore Trail Series, takes place in Ravenswood Park, featuring a scenic course through single track and carriage roads amid peak fall foliage. This classic fall trail race offers a challenging and picturesque running experience. Participants can register o..

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 invites runners to Powisset Farm in Dover, MA, for a scenic trek through Powisset Farm and nearby Noanet Woodlands. The event offers four distances—8.3, 5.6, 3.1 and 1.5 miles—catering to both experienced trail runners and newcomers. It’s part of the Barn to Run Trail..

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..