Brookline
Trail Running Calendar near Brookline 2026-2027
Explore the top trail runs near Brookline for 2026-2027! We've gathered 26 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A community 5K trail race in Hooksett that runs from Heads Pond trail through wooded conservation land to the Hooksett Public Library. A separate 0.5 mile kids fun run is available and proceeds support local youth programs.
A trail-based 5K run/walk and a 3K walking route at Mine Falls Park supporting Meals on Wheels of Hillsborough County, with a $30 registration and a 2026 event T-shirt for early registrants.
A community 5K in Jaffrey, NH offering a woods trail and a rail trail out and back. Proceeds support the volunteer Jaffrey Firefighters Company and equipment needs of the Jaffrey Fire Department.
An 18 mile out and back trail race from Windblown Ski Area in New Ipswich NH to Watatic Mountain in Ashburnham MA with steep technical terrain and a three hour turnaround cutoff.
A community 5K in Hillsborough, NH on September 20, 2026, organized by the Hillsboro Fire Department. The off-road course may be uneven and strollers are not recommended; registration runs March 25 to September 19 with a $30 fee.
Trail-based 5K obstacle course at Wasserman Park with 12 or more beginner to intermediate obstacles, limited to 200 entries and a $40 fee.
Backyard Ultra in Leominster State Forest on September 26, 2026; runners repeat a 4.167 mile loop each hour until only one remains.
Trail races and a 6 hour timed event through Assabet River National Wildlife Refuge with aid stations, cupless rules, pacer options, and proceeds supporting refuge projects.
October 2026
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.
November 2026
Test your endurance at The Hamsterwheel in New Boston, a timed loop race on a scenic rail trail offering challenges from 6 to 30 hours for individuals and teams.
A backyard ultra style last runner standing event in Winchendon MA on a 4.1667 mile loop with multiple timed formats and a fastest lap option.