Trail Running calendar near Chester 2026-2027

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.

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.

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

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.

A 23K mountain trail race in Tamworth, New Hampshire, with about 4,800 feet of climbing and a loop over the 3,478 foot summit of Mount Chocorua. The event requires mandatory safety gear and is cupless.

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.

Sunapee Scramble on June 7, 2026 is an up and down mountain race at Mount Sunapee that serves as the 2026 USATF National Classic Mountain Championship and features a $30,000 prize purse. The course is about 9.2 miles with 3,250 feet of vert..

The Otter Pond Trail Races will take place in Standish on Saturday 13 June 2026. You can run 10 kilometers.

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.