Trail Running calendar near Westwood 2026-2027

A 25th annual cross country event in Newburyport, MA on May 17, 2026 with adult and youth 3 mile races plus a kids 1/2 mile. First 250 3 mile registrants receive shirts and race day donations support the Travis Landreth Scholarship Fund.

Tough Tiger is an obstacle course event at Hampden Meadows School in Barrington, RI offering a 1.5 mile loop and a shorter adaptive course, with T shirts for early registrants, a raffle, and electronic timing.

A community 5K through the PEA trails in Exeter plus kids fun runs in three age groups, post race music, food, raffles and awards. Free babysitting is provided for children of registered 5K participants.

A 5K Fun Run at Strongwater Farm in Tewksbury on May 17, 2026 to raise funds for programs supporting people with mobility challenges. The trail course crosses corn fields and woods, with a shorter accessible route and family activities on s..

A one-day return of the Somers Summer 5K on May 17, 2026 at Field Road Park; entry is free and registration runs from August 28, 2025 to May 16, 2026. Proceeds support improvements to the park fitness trail.

A two-day 4K race on Cathleen Stone Island in Boston Harbor with individual and team entries, a short ferry ride, chip timing, and an on-island finish with dinner and beer. Funds raised support hands on science programs for Boston youth.

Trail races in Keene, NH on a revised, technical course where runners choose how many 12.5k laps to run. Natural single track and jeep roads, cupless aid stations, parking at Fuller Elementary School, and drumstick awards.

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 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 timed 20 mile hiking event on June 6, 2026 at Wompatuck State Park in Hingham, MA, set in 3,500 acres of wooded trails. The event is sold out and a wait list is maintained for openings.

A trail run of roughly 3 miles through farms and vineyards at Westport Rivers Vineyard & Winery on June 7, 2026. The event includes dinner, wine, live music, and a souvenir wine glass for race participants.

A community event at Stanley Park on June 7, 2026 featuring a 5K trail run or a one mile accessible route. Proceeds support renal medullary carcinoma awareness and related programs.

A 5.4 mile trail race through Dogtown in Rockport and Gloucester, MA featuring varied terrain and named historic trails. Runners and walkers are welcome; early registrants receive T-shirts and prizes are awarded by overall and age categorie..

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..