Trail Running calendar near Mansfield 2026-2027

A 4K race on Cathleen Stone Island in Boston Harbor with round trip ferry transport, chip timing, and a post-race dinner and beer. Proceeds support free hands-on science education for Boston youth and teams or individuals choose a day.

A Memorial Day Weekend inaugural *5k* trail run through Groton's General Field on May 24, 2026. The event supports Operation Delta Dog, which rescues and trains service dogs for veterans.

Powisset Farm Trail Run Spring on May 25, 2026 in Dover, MA offers 8.6, 5.6, 3.1 and 1.5 mile courses on a flat farm meadow and the rolling trails of Noanet Woodlands.

A 5K trail event on May 30, 2026 at Danvers YMCA Camp in Boxford with separate courses for runners and for walkers and waggers, pond and vernal pool scenery, prizes, post-race treats, and registration benefits.

Operation Mohawk Tactical 2 in Foxboro, MA offers 4, 5, and 9 mile running and rucking options. The event honors fallen service members and supports veteran and first responder suicide prevention under the mission of 22Mohawks.

A timed 5K trail race at Coogan Farm in Mystic, running through meadows, woods, and fields, with limited entry, tiered fees, an awards ceremony, and opportunities to meet Nature Center animal ambassadors.

On May 31, 2026 at Ice House Park in Woburn, MA the second annual Live Free Fun Run and Festival pairs a scenic *2.5 mile* off-road run or walk with a community festival. The festival features food trucks, a DJ, activities and tables from l..

A family friendly Monday night trail series in Nashua offering 5K and 5-mile races plus virtual options, themed evenings with music and giveaways, and occasional frozen treats at the finish.

A weekly 5K cross-country trail series at Worthington Winery in Somers, Connecticut, held Wednesdays from June 3 to July 1, 2026. The course runs through backwoods and vineyard areas with views of ponds and a covered bridge.

A community running event on June 6, 2026 in Holliston with 5K, 10K, and a Kids Fun Run on the flat Holliston Rail Trail. Registration opens March 1; fees are $30 for the 5K and 10K and $5 for the kids run.

A 20 mile single-loop hike through Wompatuck State Park near Boston on June 6, 2026, with aid stations roughly every 5 to 7 miles, finisher medals and certificates. The event is currently sold out.

A trail run at Westport Rivers Vineyard & Winery on June 7, 2026, covering about 3 miles of mixed trails and finishing among the vines. The event includes dinner, wine, music and a souvenir wine glass, with BBQ only options available.

Run for RMC on June 7, 2026 at Stanley Park in Westfield MA offers a 5K trail run and a 1 mile accessible route to raise awareness of renal medullary carcinoma and support related programs.

A ninth annual trail race through Dogtown Common on a rugged 5.4 mile course that mixes carriage roads and technical rock sections. Walkers are welcome, course maps are available, and prizes and event shirts are offered.

A five mile fun run along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on June 13, 2026. The day features food and festivities, a children's loop, return transport on request, and benefits local historical socie..

A trail event in Dunstable, MA supporting the Humane Society for Greater Nashua, featuring a marked 5-mile loop with nearly 600 ft of elevation gain per lap and an optional 6-hour format for repeated laps.

A Last Human Standing trail race near Big River Management Area in West Greenwich, RI. Runners repeat the same loop each hour and must complete each lap within 60 minutes to remain in the field until only one athlete remains.

Trail races at Mansfield Hollow State Park: a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K trail loop. Proceeds support Connecticut trail stewardship groups.

A community run on a three-loop course at the Natick Community Organic Farm, mixing trail, field, and road surfaces. Participants receive a commemorative chicken medal and top finishers are tracked in adult and kid categories.

A 5.6 K trail run and walk at Berry Pond in Harold Parker State Forest on June 14, 2026. Walkers and leashed dogs are welcome; prizes are awarded, all entrants receive a bandana, and hotdogs are provided after the race.