Trail Running calendar near Westwood 2026-2027

A multi day timed trail event on a Winchendon farm using a roughly two mile loop. Runners choose from six hour day or night, 12 hour, 24 hour, or 48 hour formats under the Sturgeon Moon.

An eight-hour trail event in Tolland, Connecticut where participants run repeated ~5K loops from Crandall's Pavilion. The day includes music, a potluck with pancakes and burgers, and proceeds that support Connecticut trail stewardship.

A 5K off-road trail run, walk, and hike at White Barn Farm through Wrentham conservation land. The event is part of the Farm to Trail 5K Series and raises funds to support local agriculture and food pantry donations.

A chip-timed 5K run/walk at Brimfield Winery on a two-lap grass course with hills, race swag, a wine pour, and age group awards; a one-lap 1.5 mile division is available.

Trail runs over Vineyard Hill and through Bradley Palmer State Park offering 5K and 10K courses with one Start/Finish aid station, local prizes, and chip timing as part of the North Shore Trail Series.

A 5K cross country race at Waters Farm in Sutton Massachusetts that opens the USATF New England XC Grand Prix series. Separate men's and women's open races, on site registration, and a post race awards ceremony.

A multi event ultramarathon in West Greenwich, Rhode Island featuring a repeated 10 mile loop with desert, pavement and trail sections. Chip timed events include aid stations, a finisher sweatshirt and a buckle for 100 mile finishers.

An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.

A timed, summit-driven trail event on Wachusett Mountain offering 7, 14, 21, and 28-mile options, optional weighted vests for bonus swag, and up to 10 hours to complete the marked course.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

Trail Animals Running Club hosts a multi distance trail event at Great Brook Farm State Park on September 5, 2026. Looped 10K and 10 mile courses cover distances from 10K to 50 miles, plus a youth fun run and a Yeti Mischief Mile.

A community 5K run and walk in Nashua, NH on September 5, 2026 with free registration for veterans and children, a fee for participants 13 and older, event shirts, donation options and volunteer opportunities. Use #nashua5k for photos.

A 5K trail run and a 1/4 mile kids fun run at Felix Neck Wildlife Sanctuary in Edgartown, MA, with scenic trails and birdlife. Proceeds benefit the sanctuary's wildlife protection, education, and conservation programs.

Trail ultramarathon and half marathon in Bear Brook State Park near Allenstown, NH. The ultra varies between 50k and 100k and is navigated with GPX files only; aid stations do not provide cups.

An unsupported, end-to-end group run of about 56 miles along the Farmington Canal Heritage Trail from West Suffield to New Haven, organized as a fundraiser for Mental Health Connecticut with a 14 hour completion limit and required self-supp..

A Keene State College alumni cross-country meet on 09/12/2026 at the Keene State Athletic Complex featuring a men's 5K and a women's 2 Mile race; registration runs 09/06 to 09/12 with a $25 fee per event.

Thunder Run is a 5K trail race with more than 20 obstacles through woods and hills in Candia, New Hampshire on September 12, 2026. Organized by Raymond Area Rotary, 100% of proceeds support local and selected international projects.

Pisgah Mountain Trail Races in Chesterfield, NH offers 50k and 23k mountain trail ultraruns on Sunday 9/13/26. Aid stations provide LMNT, Tailwinds, and Untapped and proceeds support New Hampshire Special Olympics.

GBTC XC Invite in Carlisle, MA features youth and Open/Masters cross-country races at Great Brook Farm State Park on September 13, 2026. Distances include a 2K youth race and multiple 5K races; registration runs August 1 to September 11.

A free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.