Chesterfield
Trail Running Calendar near Chesterfield 2026-2027
Explore the top trail runs near Chesterfield for 2026-2027! We've gathered 6 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Family oriented 5k trail run and free fun walk at Chesterfield Gorge with handmade hat prizes, locally baked cookie medals, and a community potluck.
April 2027
A long running weekly 5 km cross country series in Northampton with day of registration, an accurately measured course through fields and woods, and a season pass option.
Trail event at The Hartsbrook School in Hadley MA featuring a 5K trail run or walk and a 1 mile Mushroom Mile with proceeds supporting school programs.
June 2027
Point to point trail event along the New England Trail with 112 and 50 mile options; requires crew support, blue blaze navigation, and technical terrain.
July 2027
Notchview Ultra in Windsor, MA (July 9-12, 2027) uses a 1.9 mile loop and offers a 100.7 mile race plus multiple timed events with on-course aid and on-site amenities.
October 2027
A 24 hour invitational loop race at Notchview in Windsor MA with a 1.9 mile course, minimal aid support, camping options, and proceeds benefiting the Trustees of Reservations.