Trail Running calendar near Cumberland 2026-2027

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

Run a unique 4K trail race on Cathleen Stone Island in Boston Harbor, accessed by a short ferry ride. The two-day event supports free science education for local youth and features a post-race party. Choose to run individually or with a cor..

Trail races at Powisset Farm in Dover MA run through farm fields and Noanet Woodlands with four distances from 1.5 to 8.3 miles. One aid station provides water and this is a cupless race so runners must bring their own hydration carrier.

The Wildcat 5K Trail Run-Walk-Wag is a trail event on May 30, 2026, featuring separate courses for runners and walkers around Wildcat State Forest. Starting at Danvers YMCA Camp overlooking Stiles Pond, the event offers prizes, treats, and..

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 point-to-point ultramarathon on the New England Trail offering 112-mile and 50-mile options to Guilford. Entrants must make a donation to the Connecticut Forest and Parks Association and arrange their own crew and navigation.

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.

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.

Run a scenic 3-mile trail through vineyards and farms at Westport Rivers Winery. After the race, enjoy a dinner with wine and live music. All runners receive a souvenir wine glass.

A trail event in Dunstable MA featuring a marked 5-mile loop with about 600 feet of elevation per loop and a 6-hour option to run multiple laps; proceeds benefit the Humane Society for Greater Nashua.

A trail running event at Mansfield Hollow State Park offering a 15.7 mile out-and-back on the Nipmuck Trail and a new 5K course entirely inside the park. Proceeds support Connecticut trail stewardship groups.

Early morning trail run in Gay City State Park offering 3, 5 and 8 mile races. The 8 mile is part of the Blue Blazed and USATF CT MUT series and includes teams of three competing for prize money.

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..

The TARC Blue Hills Skyline Trail Run will take place in Canton on Saturday 11 July 2026. You can run 12 kilometers.

A unique trail race at Soapstone Mountain featuring six ascents. Runners circle the base and climb each upward trail they find, finishing with the infamous Killer Hill. The challenging course includes rocky and steep terrain.

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

The Tarc Summer Classic will take place in Medfield on Saturday 8 August 2026. You can run between 10 and 40 miles.

Run trails on a 5 km loop for 8 hours at Crandall's Park. It's a potluck celebration with food, raffles, and games. Complete loops to earn tickets for prizes and a commemorative gift.

The Watermelon Wobbler is a 5k trail run/walk/hike through scenic conservation land and a working farm. It features a varied off-road course and supports local agriculture. On-site parking is supplemented by a satellite lot nearby.

The annual Vineyard Hill Trail Run features a scenic 5K/10K course over Vineyard Hill and through Bradley Palmer State Park. It's part of the North Shore Trail Series and includes a fully marked trail with an aid station.