Trail Running calendar near Brookline 2026-2027

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.

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.

Experience the beauty of the Ashuwillticook Rail Trail with a marathon, half marathon, or 8K race. This annual event includes USATF certified courses, finisher medals, and a dedicated kids run for families.

Cross country 5K at Cole's Family Farm in Dayton on May 16, 2026 supporting the Southern Maine Young Marines. Options include a 1.25K fun run and a 5K ruck march; entry includes a patriotic t-shirt and participation medal.

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.

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..

Test your endurance at the Ascutney Mountain Run in Vermont. This 3.7 mile uphill race climbs 2,300 vertical feet along a paved auto road to a scenic mountain summit finish.

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.