Trail Running calendar near West Windsor 2026-2027

Trail races in Groton, Massachusetts on October 4, 2026, organized by local running and trails groups. Two distances, 9.5 miles and 3.4 miles, total entries limited to 250, online registration closes October 3.

Keene Family YMCA Fall Foliage Trail Races feature 5K and 10K trail courses starting and finishing at the Keene YMCA, with chip timing, age-group prizes, and proceeds supporting YMCA programs and access.

A one-mile charity run at Gunstock Mountain Resort on October 4, 2026, benefiting Big Brothers Big Sisters of New Hampshire & Vermont. Online registration closes October 2; adult and teen entries are $20, children under 12 enter free.

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 is a trail event on Wright's Mountain in Bradford, VT on October 10 and 11, 2026. Runners complete laps of a 10K loop on mixed rocky and rooty terrain, with a 100 runner cap and themed tarot awards.

A rugged trail race at Pawtuckaway State Park featuring technical terrain, boulders, streams and a rocky climb. It offers a half marathon and a 5 mile option and lists $7500 in prize money for 2026.

Trail marathon and half marathon at Trapp Family Lodge in Stowe, VT. A 13.1 mile loop mixes runnable trails, single track and steep climbs, including a climb to Round Top Mountain amid autumn foliage.

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.

A mountain running event in North Conway, NH on October 17, 2026, featuring two race options on Cranmore Mountain and $7500 in cash prizes. The course uses ski slopes, singletrack, and service roads and includes one aid station.

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.

A mountain trail race in Keene NH on October 25, 2026 covering 4.9 miles with 1,650 feet of elevation across four laps; the event benefits the Keene Community Kitchen and offers prize money, age-group awards, and raffles.

A technical 14 mile trail race at Moreau Lake State Park in Gansevoort, NY, featuring about 2700 feet of gain on winding singletrack and one aid station near Bonita Lake. The route starts and finishes at the park beach.

A 36 hour community trail festival at Catamount Outdoor Family Center in Williston, VT featuring two repeating 3 to 4 mile loops with views of Camel's Hump and Mt. Mansfield. Entry is donation based and participants help at the aid station.

A multi hour loop event on the New Boston Rail Trail near the fairgrounds offering 6, 12, 24 and 30 hour individual and relay options, chip timing, a central aid station, team entries, pacer rules and 100-mile buckles.

A backyard ultra at Kenty's Farm on November 7, 2026 where runners complete repeated 4.1666 mile laps until one remains; also offers 6, 12 and 24 hour timed options and a single-lap competition.

A mountain race at Cranmore Resort on November 7, 2026, offering 5 km and 10 km courses on access roads and ski trails, marked with reflective flagging and LED lanterns; headlamps are required and registration is online.

A Last Person Standing mountain event with hourly 2.25 mile laps that climb about 1,209 feet each. Aid, hot food, camping, elevation milestone prizes, and awards are provided; conditions may include cold, snow, or ice.

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.

A Thanksgiving morning trail event in Jackson, New Hampshire featuring a 5k through nordic trails and a 1k kids run for ages 10 and under. Day of registration is available and proceeds benefit local youth programs.

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..