Trail Running calendar near West Windsor 2026-2027

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.

The Devil's Den Ultra challenges runners on a rugged 6.4-mile Vermont trail loop. Choose from a 30-hour, 12-hour, or single-loop 10K race. Every finisher earns a unique Devil tarot card, with more cards awarded for major milestones in the t..

Vulcan's Fury Trail Race The Vulcan's Fury Trail Race takes place in Pawtuckaway State Park in Nottingham, New Hampshire. It is a rugged trail race on a course described as very technical and scenic. Two distances are offered: a Half Marath..

A fall trail marathon and half marathon on the scenic Trapp Lodge trail system in Stowe, Vermont. The course features a mix of wide paths and rugged single track with significant climbs and descents. Participants will run through the colorf..

Run through history on New Hampshire's Granite Town Rail Trail. This October event offers races from a 15-mile run to a 30-hour ultramarathon, all benefiting local trail conservation. The fall foliage creates a memorable backdrop for this u..

The Cranmore Mountain Race is a classic two lap mountain run in New Hampshire. Runners tackle ski slopes and trails for a share of $7500 in prizes. This historic event is part of the USATF New England Mountain Circuit.

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.

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.

The Moreau Half on October 31, 2026, tackles 14 miles of technical singletrack in Moreau Lake State Park, featuring 2,700 feet of elevation gain. With a start and finish at the park beach, this challenging trail run includes one aid station..

Test your endurance at this backyard ultra in Winchendon featuring a 4.1666 mile loop through fields and trails. Choose from the last runner standing format, timed races, or a single lap challenge in a relaxed community setting.

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..