Trail Running calendar near Rockport 2026-2027

Join this adventure based event in Barrington featuring a 1.5 mile neighborhood loop and an accessible adaptive course. This family focused run includes electronic timing and performance shirts for the first 1,000 participants.

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 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.

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.

Run or walk through the scenic Wildcat State Forest Trail in Boxford. This bird friendly event features separate courses for runners and walkers starting at the Danvers YMCA Camp overlooking Stiles Pond.

Operation Mohawk Tactical 2 unites the Mohawks Medevac and Honor & Remember 5 Miler events. It takes place at F Gilbert State Forest in Foxboro, supporting veteran and first responder suicide prevention. Participants can run, ruck, walk, or..

A scenic 2.5 mile off-road run or walk around Horn Pond paired with a festival at Ice House Park featuring food trucks, a DJ, raffles, kids activities, and over 25 local mental health and substance use providers.

A themed Monday night in the Mine Falls Summer Trail Series at Stellos Stadium, featuring 5K and 5 mile options, music, giveaways and both in person and flexible virtual participation.

Run a flat, out-and-back course on the scenic Holliston Rail Trail. This event offers a 5K and a 10K for adults, plus a fun run for kids with distances based on age. The community gathering point is Blair Square in Holliston.

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.

Enjoy a 3 mile trail run through the scenic Westport Rivers Vineyard & Winery followed by a vineyard celebration with dinner, wine, and live music.

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 the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.

Experience a scenic New England trail event in Dunstable with a 5 mile loop or a 6 hour timed challenge. Support the Humane Society while running through historic quarries and former ski hills.

Run a scenic yet rugged half marathon trail race at Lynn Woods Reservation in Massachusetts. This 13.1-mile event features three challenging loops showcasing the historic Stone Tower. The focus is on sustainability and a centralized start/f..

Experience a 5k obstacle mud run designed for unity and women empowerment at Kimball Farm in Haverhill. Join a supportive community for a day of teamwork and mud while supporting the National Breast Cancer Foundation.

A three-race summer trail series at West Hill Dam featuring well-marked wooded single and double-track trails, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

A Spartan obstacle race weekend at Carter & Stevens Farm in Barre, MA, featuring a Sprint 5 km with 20 obstacles, a Super 10 km with 25 obstacles, and kids races. The farm venue includes mud, woods, rolling hills and a farm store.