Trail Running calendar near Berkley 2026-2027

Celebrate the eighth annual Trillium Spring 5K in Canton or participate virtually from anywhere. Join over 500 runners at the brewery to support Girls on the Run Greater Boston with races for adults and children.

Wason Pond Wrangler is a family friendly obstacle course trail race around Wason Pond in Chester, New Hampshire with a *5K* route and more than ten obstacles. The event raises funds for local nonprofits and welcomes individuals and teams.

Trail races at Soapstone Mountain in Stafford Springs, CT include a new half marathon and the Jerry Stage 6K Sampler. Courses run on the blue blazed Shenipsit Trail through Shenipsit Forest with on course aid for the half marathon.

The Trav's Trail Run will take place in Newburyport on Sunday 17 May 2026. You can run 3 miles.

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.

Experience a scenic trail run through the Phillips Exeter Academy woods. This event features a 5K race for all ages and specific fun runs for children 12 and under with on site activities and childcare.

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 community campus event in East Haddam featuring a 1.75 mile looped course with rocky dirt paths, kids races on the soccer field, reused-trophy awards, dog-friendly provisions, and water stops on a rain or shine race day.

Experience a unique trail race on Cathleen Stone Island in the Boston Harbor. Enjoy a scenic ferry ride and a chip timed run followed by dinner and drinks to support science education 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..

Experience a timed 5K trail race through the scenic meadows and woods of Coogan Farm in Mystic. Enjoy post race festivities with animal ambassadors and support local environmental conservation at this inaugural event.

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 in Nashua offering in-person and flexible virtual options, with 5K and 5 Mile routes, music, giveaways, photos, and occasional frozen treats at the finish.

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.

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

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.

Trail races at Mansfield Hollow State Park include a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K single track loop; proceeds benefit Connecticut trail stewardship and the event is organized by the Shenipsit Striders.