Hillsborough
Trail Running Calendar near Hillsborough 2026-2027
Explore the top trail runs near Hillsborough for 2026-2027! We've gathered 14 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Trail ultramarathon and half marathon at Bear Brook State Park with GPX navigation, minimal markings, no cup aid stations, and variable ultramarathon distance.
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 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.
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.
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 5-mile mountain trail race at Granite Gorge with four laps and about 1650 feet of elevation, held to benefit the Keene Community Kitchen.
November 2026
Hugs From Vets Trail 10Kish in Henniker, New Hampshire on November 1 features a mixed trail and country road course and raises funds for American Legion Post 78. The field is limited to 150 participants and awards are given to overall and age group t..
Timed loop event in New Boston NH offering 6, 12, 24 and 30 hour individual and relay options with chipped bib tracking and a central aid station.
February 2027
Two-day national snowshoe championships in Concord NH with 10K and 5K races, age-group awards, and fleece blankets for top finishers.