Brookline
Trail Running Calendar near Brookline 2026-2027
Explore the top trail runs near Brookline for 2026-2027! We've gathered 28 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A community fundraising day in Groton, MA on August 5, 2026 featuring an 8.4 mile three-person relay, kids single-loop race and Little Lambs mini runs, followed by barbecue and activities, with proceeds to six local charities.
A community 5 km run in Derry, New Hampshire on August 8, 2026, with adult and kids categories and online registration closing August 7, 2026.
A timed, summit-driven trail event on Wachusett Mountain offering 7, 14, 21, and 28-mile options, optional weighted vests for bonus swag, and up to 10 hours to complete the marked course.
September 2026
Trail Animals Running Club hosts a multi distance trail event at Great Brook Farm State Park on September 5, 2026. Looped 10K and 10 mile courses cover distances from 10K to 50 miles, plus a youth fun run and a Yeti Mischief Mile.
A community 5K run and walk in Nashua, NH on September 5, 2026 with free registration for veterans and children, a fee for participants 13 and older, event shirts, donation options and volunteer opportunities. Use #nashua5k for photos.
Thunder Run is a 5K trail race with more than 20 obstacles through woods and hills in Candia, New Hampshire on September 12, 2026. Organized by Raymond Area Rotary, 100% of proceeds support local and selected international projects.
GBTC XC Invite in Carlisle, MA features youth and Open/Masters cross-country races at Great Brook Farm State Park on September 13, 2026. Distances include a 2K youth race and multiple 5K races; registration runs August 1 to September 11.
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 race at Wasserman Park on September 26, 2026 featuring 12 or more beginner and intermediate obstacles and limited to 200 participants.
Trail races at the Assabet River National Wildlife Refuge in Sudbury MA include a 10K, a 30K and a 6 hour timed event. The course uses dirt and gravel double track trails with two aid stations and cupless fueling.
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.
Trail event in Brookline, NH with multiple races on the Granite Town Rail Trail and proceeds supporting local conservation.