Trail Running calendar near Henniker 2026-2027

A 4K race on Cathleen Stone Island in Boston Harbor with round trip ferry transport, chip timing, and a post-race dinner and beer. Proceeds support free hands-on science education for Boston youth and teams or individuals choose a day.

Morning trail runs for women and nonbinary participants around the North Reservoir in Winchester, MA. A conversational 3-mile loop that takes about one hour; sessions cancel for steady rain or thunder.

Trail races in Keene, NH using a 12.5K loop that can be repeated for 12.5K, 25K, 37.5K, or 50K. The course is technical single track and old jeep roads with aid stations, drop bag access, and portable toilets.

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.

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 running event in Granville on May 30, 2026: a relatively flat 5k along the rail trail finishing on the footbridge over the Mettowee, plus a kids 1k. Registration opens March 26; 5k fee $25, kids run free.

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.

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 trail event in Bradford, Vermont on June 6, 2026 featuring a 5K that climbs to Wrights Mountain summit and a 1.5 mile fun run for ages 13 and under. Proceeds support the Friends of Wrights Mountain Fund.

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 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 ninth annual trail race through Dogtown Common on a rugged 5.4 mile course that mixes carriage roads and technical rock sections. Walkers are welcome, course maps are available, and prizes and event shirts are offered.

A 6.9 mile trail race at Cannon Mountain on June 13, 2026 with 3,080 ft of elevation gain and a 4,031 ft summit. The marked course includes steep ridge and ski-trail sections and is capped at 500 runners with a 2 hour summit cut off.

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.