Trail Running calendar near Derry 2026-2027

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.

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 Monadnock State Park, featuring over 6,000 feet of elevation gain. The course mixes roads, dirt roads, and trails, and requires GPX navigation. With limited spots, runners must plan..

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.

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.

Choose your own adventure at the Drummer Hill Trail Races in Keene, NH. Run a flexible number of 12.5k laps on technical, hilly trails, with distances from 12.5K to 50K. Aid stations and a cupless policy support your run through scenic wood..

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.

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.

The Chocorua Mountain Race is a rugged 23K adventure in New Hampshire's White Mountains, featuring 4,800 feet of climbing over rocky trails to the summit of Mount Chocorua. It kicks off the White Mountain Endurance Cup series. Runners must..

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.

The Sunapee Scramble is a two-lap mountain race at Mount Sunapee Resort, featuring 9.3 miles and 3,300 feet of climbing. It hosts both the USATF and Collegiate Mountain Running National Championships in 2026. The event also includes the New..

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

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.