Trail Running calendar near Westwood 2026-2027

A trail race on Winant Park Trails near downtown Concord with windy singletrack, switchbacks, and nordic type paths. Two distances are offered and proceeds benefit the Ralph Waldo Emerson School for Preschoolers; day of event entry is avail..

Trail races at Watuppa Reservation in Fall River on May 9, 2026, featuring grassy fire lanes, winding single track and aid stations each lap. Distances offered are 10K, 30K and 50K.

Trail races in Rollinsford, NH along the Salmon Falls River, offering a canicross 5K, a 5K, and a 5 Miler. Courses mix rail trail, single track, and open fields, with an aid station and specific rules for dog teams.

Experience the varied landscapes of Block Island with a 10K course featuring coastal tracks and rolling pastures. Running through diverse terrain this spring event includes a steep double tiered climb and views of the Atlantic.

Join the community at the Pinkerton Academy 5K Astro Run in Derry New Hampshire for a scenic 5 km race held on the academy campus grounds.

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

A point to point 50 mile ultramarathon from Manchester to Mount Monadnock with about 6000 feet of gain, mixed road and trail terrain, GPX only navigation, five aid stations, a 125 runner cap, and no organized shuttle service.

Run or walk a 5k on the Southern New England Trunkline Trail in Franklin. This event supports the development of an abandoned rail bed into a multi use path connecting local communities.

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.

New for 2026, the Soapstone Mountain Trail Races in Stafford Springs feature an all new half marathon route over Soapstone Mountain and a Jerry Stage 6K sampler, both running on sections of the blue-blazed Shenipsit Trail with proceeds to l..

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.

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 trail race in Keene NH on May 23, 2026 using a 12.5k loop system with options up to 50K. The unpaved course features technical single track, jeep roads, cupless aid stations, drop bags, and parking at Fuller Elementary.

Experience a scenic trail race through the historic Powisset Farm and Noanet Woodlands. Choose from four distances featuring grassy farm paths and forested trails including a climb up Noanet Peak.

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..