Trail Running calendar near Keene 2026-2027

Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.

Devil's Den Ultra in Bradford, Vermont on Oct 10 to 11 2026 uses a 10K loop on Wrights Mountain and offers 30 hour, 12 hour and 10K options. Entries are capped at 100 and finishers receive tarot style awards.

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

Vulcan's Fury Trail Race at Pawtuckaway State Park offers a half marathon and a 5 Miler over technical trails with boulder fields, switchbacks, stream crossings and a rocky ridge called the Devil's Staircase. Three aid stations support runn..

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

Experience New Hampshire’s original 30 hour ultramarathon on the historic Granite Town Rail Trail. Choose from multiple distances and relay options in this flat and fast Halloween themed fundraiser for local trail conservation.

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All proceeds support local trail maintenance.

Run a scenic autumn 5k trail through Wrentham conservation land and a working farm. This cup-less race supports local agriculture and includes family Halloween fun. It's the final event of the Farm to Trail 5K Series.

Fall trail races on rugged single-track at Mt. Tom State Park include a 25k, 2-person 25k relay, 10k and a 5k fun run with significant climbing and proceeds benefiting Kestrel Land Trust.

Tackle a unique mountain course that goes up and down four times over 4.9 miles. The event offers prize money, age group awards, and benefits the Keene Community Kitchen. Early registration includes a t-shirt.

This fall trail run takes place at Powisset Farm in Dover, MA, featuring four scenic distances through farm and woodland trails. Post-race cider donuts and family activities like pumpkin painting add to the farm atmosphere. It's part of the..

A technical trail half marathon at Moreau Lake State Park near Gansevoort, NY, covering about 14 miles with 2700 feet of climbing and one aid station; start and finish are at the park beach.

Experience an obstacle course race inside the historic Fenway Park stadium. This event features a 5K course with 20 obstacles and dedicated races for children through the iconic home of the Boston Red Sox.

The Hamsterwheel in New Boston NH is a multi hour timed ultrarun with 6 12 24 and 30 hour options on a 4.0 mile loop along the New Boston Rail Trail and around the fairgrounds. Central aid and chip timing support lap tracking.

Experience a classic New England trail event at Willowdale State Forest featuring multiple distances from 10K to 100K. Run through rolling terrain on a course celebrated for its community spirit and long history.

A backyard ultra at Kenty's Farm on a 4.1666 mile loop where runners repeat hourly laps until one remains. Timed options of 6, 12 and 24 hours and single-lap entries are also available.

TARCkey Trot is a 6 hour trail challenge at Wright Locke Farm of repeated 5K loops with rocky rollers. Run as many loops as you wish and bring your own hydration for this cupless event.

A Last Person Standing uphill event on Mount Ascutney near Brownsville, VT, featuring hourly 2.25 mile laps with about 1,209 ft of gain, one aid station, indoor facilities, camping, awards, and local donations.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

TARC Winter Classic in Stoneham offers 8, 32 and 40 mile trail races on the white blazed Skyline Trail with rugged roots, rocks, frequent climbs and Boston skyline views. Expect technical trails, minimal markings and a festive finish.