Roxbury
Trail Running Calendar near Roxbury 2026-2027
Explore the top trail runs near Roxbury for 2026-2027! We've gathered 17 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
An inclusive trail festival at Northfield Mountain offering a 20k prediction run, an untimed 5k fun run/hike (about 6k), a kid's run, and a virtual option.
September 2026
Three community races at Springfield Dam include a free kids 0.5 mile, a 1 mile Maniac Mile for ages 10 and up, and a scenic 3.1 mile course with trails, food vendors, and family activities.
Pisgah Mountain Trail Races in Chesterfield, NH offers 50k and 23k mountain trail ultraruns on Sunday 9/13/26. Aid stations provide LMNT, Tailwinds, and Untapped and proceeds support New Hampshire Special Olympics.
A 1 mile inflatable fun run and walk at Butterfield Park in Orange, MA raising funds for Fisher Hill School sixth grade trip fundraising, with advance registration at $15.
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.
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 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.
A backyard ultra at Kenty's Farm in Winchendon MA on Nov 7 2026 featuring a 4.16667 mile loop plus 6, 12 and 24 hour timed options.
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.