Trail Running calendar near Ipswich 2026-2027

Discover the beauty of Emmons Preserve at a community event featuring trail races and family activities. Enjoy music and local treats while supporting holistic education through a variety of distances for runners and walkers.

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.

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.

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.

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.

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 offers 8 32 and 40 mile trail races on the rugged Middlesex Fells Skyline Trail with roots, rocky climbs and occasional Boston skyline views. Affordable entry and proceeds support land conservation.

Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.

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.