Brookline
Trail Running Calendar near Brookline 2026-2027
Explore the top trail runs near Brookline for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes with snacks.
Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.
Inaugural trail event in Dublin NH with a 5K and a 1 mile kids fun run on October 10, 2026 supporting the Dublin Consolidated School PTO.
A multi format trail event on the Granite Town Rail Trail in Brookline and Milford NH on October 17 and 18 2026, featuring 7.5 mile relays, 15 mile and 30 mile races and a 30 hour ultramarathon. Proceeds support local trail conservation.
A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.
A fall festival in Tyngsboro featuring a 3K trail race, a free kids fun run for ages 7 and under, a farmer’s market, vendors, kids activities, and food on October 25.
Trail races at Assabet River National Wildlife Refuge in Sudbury MA with 10K, 30K and a 6-hour timed loop event on dirt and gravel double-track trails.
November 2026
A backyard ultra weekend at Kenty’s Farm with a 4.16667 mile loop, Last Runner Standing format, and timed 6/12/24/48-hour events plus themed community hours.
Timed loop running events in New Boston, NH with a 4.0 mile loop and options from six to thirty hours, chip timing, relays, teams, and a central aid station.
Trail 5K at Temple Mountain Reservation featuring a double summit via the Wapack and Beebe Trails, one aid station, spectators welcome and no pets allowed.
Third annual Thankful Trails 5K at Windham Woods School on November 14, 2026, features a two loop trail 5K and a free kids fun run on the lower field.
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.
A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.
A 4 mile trail race in Mine Falls Park with a post race party, raffle, awards, and proceeds supporting the Nashua Children's Home.
April 2027
USATF sanctioned 10 mile trail race in Andover MA with timed results, aid stations, baked prizes, and proceeds supporting Merrimack River Trail maintenance.
May 2027
Trail ultramarathons on the Wapack Trail in Ashburnham, MA with 21.5, 43, and 50 mile options over rocky, technical terrain and significant elevation gain.
August 2027
A timed, single-day endurance walk on Wachusett Mountain with 7, 14, 21, or 28 mile loops, optional weighted rucks, and aid stations about every 2.5 to 3 miles.