Windham
Trail Running Calendar near Windham 2026-2027
Explore the top trail runs near Windham for 2026-2027! We've gathered 13 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A six hour timed trail race on a rocky 5K loop at Wright Locke Farm with a cupless aid station, goat companions, a $35 entry, and limited registration.
Community 5K and kids fun run at Windham Woods School with trail loops, a raffle, onsite lunch, and limited field of 200 participants.
A community trail event at Good Pickin’ Farm with a scenic 5 mile run, a 2.5 mile walk or run, and a 1K kids run plus post race farm activities.
Community cross country walk and 5K at the Academy of Notre Dame in Tyngsboro on November 21, 2026, raising funds for a science lab and scholarship.
A 4 mile trail race in Mine Falls Park followed by a post-race party, raffle, and awards at Martha's Exchange, with proceeds supporting the Nashua Children's Home.
A trail 5K at Maudslay State Park merged with the Run For Pie event, with 100% of profits donated to local food charities and early shirt pick-up options.
A 5K and 1 mile Kids Fun Run at Patton Park on November 28, 2026, featuring age divisions, prizes, a Boston Marathon entry giveaway, and packet pick up options.
December 2026
A 20th edition December event in Melrose featuring a changing 3.5 mile cross-country race and a 2 mile non-competitive walk with team and individual awards.
March 2027
April 2027
Ten mile trail race along the Merrimack River in Andover with USATF sanction, post race refreshments, awards, and proceeds supporting local trail maintenance.
October 2027
Point to point autumn trail ultramarathon across the Midstate Trail in Massachusetts offering 100 mile, 50 mile and 50 km options; 100M and 50M carry UTMB Index status.