Brookline
Trail Running Calendar near Brookline 2026-2027
Explore the top trail runs near Brookline for 2026-2027! We've gathered 11 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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.
February 2027
A 3.8 mile out and back trail race from Monadnock State Park Headquarters to the summit via White Dot Trail, raced in winter conditions with a three hour cutoff.
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.
May 2027
A technical trail event on the Wapack Trail in Ashburnham MA offering 21.5, 43 and 50 mile options with rugged terrain and significant climbing.
August 2027
A single day endurance walk on Wachusett Mountain with 7 to 28 mile options, optional weighted rucks, aid stations, and a 10 hour completion window for official recognition.
October 2027
Ever Onward is a timed trail event in Dublin NH with three, six, nine or twelve hour options on a 4.5 mile loop through grassy paths and single track.
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.