Chesterfield
Trail Running Calendar near Chesterfield 2026-2027
Explore the top trail runs near Chesterfield for 2026-2027! We've gathered 4 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
November 2026
A family friendly 5k trail run and fun walk at Chesterfield Gorge with handmade hat prizes, cookie medals and a community potluck supporting Hilltown Land Trust.
April 2027
Trail event in Hadley MA on April 25, 2027 with a 5K and a one mile Mushroom Mile, on-campus trails, a virtual 5K option, and proceeds to The Hartsbrook School.
June 2027
Point-to-point trail event on the New England Trail offering 112-mile and 50-mile routes to Guilford, CT, with self-supported crews and route navigation required.