Trail Running calendar near Wayland 2026-2027

Experience the rolling trails of Willowdale State Forest at this long running festival. With distances from 10K to 100K, runners enjoy a supportive community atmosphere and scenic single track paths in Massachusetts.

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.

A trail race at Burlingame State Park in Charlestown on November 15, 2026, offering 4-mile and 8-mile courses around Watchaug Pond. It is the first race in the WTAC fall trail series with multi-race registration discounts.

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.

Experience a unique cross country tradition at the Mount Hood Golf Club with a hilly 3.5 mile run or a festive 2 mile walk. Compete for nutcracker awards and enjoy a post race pasta lunch for a good cause.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.