Windsor
Trail Running Calendar near Windsor 2026-2027
Explore the top trail runs near Windsor 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
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
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 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.
May 2027
A six hour loop ultra on May 1, 2027 at Jug End State Reservation in Egremont, MA where participants complete as many 3 mile laps as they can while supporting local charities.
July 2027
Trail ultrarunning at Notchview in Windsor MA on a 1.9 mile loop, with options from 6 hours to 100.7 miles and on course aid and campsite support.
October 2027
Notchtoberfest is a 24 hour invitational trail event at Notchview in Windsor MA with a 1.9 mile loop, camping, self timed laps, limited aid, and proceeds to the Trustees.