Trail Running calendar near Chester 2026-2027

Experience the seasonal scenery of New Hampshire at the Keene Family YMCA Fall Foliage Trail Race. Choose between a fast 5K or a 10K with elevation gain to support local community programs.

The Mile for Mentoring will take place in Gilford on Sunday 4 October 2026.

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.

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 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.

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.

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.

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.

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.

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.

Race Mozey brings the Central European Krampus Run tradition to New England. Choose from a 5K, 10K, or a 9-hour challenge to complete laps at the Dartmouth Skiway. Finishers get medals, and the event supports Vermont Adaptive Ski and Sports..