Trail Running calendar near Bedford 2026-2027

A Memorial Day Weekend inaugural *5k* trail run through Groton's General Field on May 24, 2026. The event supports Operation Delta Dog, which rescues and trains service dogs for veterans.

Powisset Farm Trail Run Spring on May 25, 2026 in Dover, MA offers 8.6, 5.6, 3.1 and 1.5 mile courses on a flat farm meadow and the rolling trails of Noanet Woodlands.

A 5K trail event on May 30, 2026 at Danvers YMCA Camp in Boxford with separate courses for runners and for walkers and waggers, pond and vernal pool scenery, prizes, post-race treats, and registration benefits.

Operation Mohawk Tactical 2 in Foxboro, MA offers 4, 5, and 9 mile running and rucking options. The event honors fallen service members and supports veteran and first responder suicide prevention under the mission of 22Mohawks.

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 choose your own adventure ultra and trail event at Chesterfield Gorge with multiple distances, lap based 50k to 100mi options, a 30 hour window for ultras, and timed 33k and 11k races the following day.

Run of The Fellowship is an in-person trail event at Clifford Park in Biddeford, Maine on May 30, 2026. It offers a 5K route and a longer full quest option, welcomes costumes, and is pending final permits and insurance.

On May 31, 2026 at Ice House Park in Woburn, MA the second annual Live Free Fun Run and Festival pairs a scenic *2.5 mile* off-road run or walk with a community festival. The festival features food trucks, a DJ, activities and tables from l..

A family friendly Monday night trail series in Nashua offering 5K and 5-mile races plus virtual options, themed evenings with music and giveaways, and occasional frozen treats at the finish.

A 23K mountain trail race in Tamworth NH with roughly 4,800 feet of climbing, a technical loop over the 3,478 foot summit of Mount Chocorua, mandatory mountain safety gear, and inclusion in the White Mountain Endurance Cup.

A community running event on June 6, 2026 in Holliston with 5K, 10K, and a Kids Fun Run on the flat Holliston Rail Trail. Registration opens March 1; fees are $30 for the 5K and 10K and $5 for the kids run.

A timed 20 mile hiking event on June 6, 2026 at Wompatuck State Park in Hingham, MA, set in 3,500 acres of wooded trails. The event is sold out and a wait list is maintained for openings.

A two-lap mountain race at Mount Sunapee Resort on June 7, 2026, covering about 9.3 miles and 3,300 feet of climbing. Hosts the 2026 USATF and Collegiate Mountain Running Championships and offers $30,000 in cash prizes.

A 5.4 mile trail race through Dogtown in Rockport and Gloucester, MA featuring varied terrain and named historic trails. Runners and walkers are welcome; early registrants receive T-shirts and prizes are awarded by overall and age categorie..

A five mile fun run along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on June 13, 2026. The day features food and festivities, a children's loop, return transport on request, and benefits local historical socie..

A trail event in Dunstable, MA supporting the Humane Society for Greater Nashua, featuring a marked 5-mile loop with nearly 600 ft of elevation gain per lap and an optional 6-hour format for repeated laps.

Trail races of 50k, 30k and 10k through western Massachusetts hill towns on single track and dirt roads, held in partnership with Franklin Land Trust and featuring aid stations, first aid and locally produced awards.

A trail race in Newport, New Hampshire on June 13, 2026 offering 6 and 3 mile routes through rocky, rooty, hilly forest trails. Proceeds support Newport Recreation and town forest trails and awards are pure New Hampshire maple syrup.

Part of the Grit Series, this Dublin NH trail event offers a 10K and a half marathon with substantial elevation gain and views of Mount Monadnock. Registration runs from May 3 to June 6, 2026.

A trail half marathon in Lynn Woods Reservation on June 21, 2026, run as three identical loops over forested singletrack and carriage roads. The event emphasizes environmental stewardship and uses a centralized start and finish at the main..