Windham

Trail Running Calendar near Windham 2026-2027

Explore the top trail runs near Windham for 2026-2027! We've gathered 23 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

December 2026

Dec

Mount Hood Nutcracker Challenge

Melrose | 26 mi from Windham

Trail Run 4 mi

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.

March 2027

Mar

Tortoise and the Hare Trail Race

Salisbury | 22 mi from Windham

Trail Run 3 mi 6 mi

Trail races and a 1 mile Color Run in Salisbury on March 27, 2027, featuring 10K, 5K and a non timed color run, with proceeds supporting Salisbury Parks and Recreation.

April 2027

Apr

Merrimack River Trail Race

Andover | 13 mi from Windham

Trail Run 10 mi

USATF sanctioned 10 mile trail race in Andover MA with timed results, aid stations, baked prizes, and proceeds supporting Merrimack River Trail maintenance.