Roxbury
Trail Running Calendar near Roxbury 2026-2027
Explore the top trail runs near Roxbury 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.
August 2026
Timed 6 hour and 12 hour loop races in Chester, Vermont on mixed single and double track trails with basic aid and town park amenities.
A 4.61 mile trail race at Moody Park in Claremont NH featuring narrow single track, wet sections and a steep drop and climb at Gravity Cavity. The event is part of the Western NH Trail Running Series and benefits the local parks department.
An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.
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.
Experience a fun inflatable obstacle course at Butterfield Park. This 1 mile run or walk supports 6th grade students at Fisher Hill School in reaching their educational trip goals through community participation.
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 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 4.9 mile mountain trail race in Keene, NH featuring four up and down laps on varied ski and single-track trails, with proceeds and food donations benefiting 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 6, 12, 24 and 30 hour loop events on the New Boston Rail Trail with a 4.0 mile marked loop, central aid station, and awards for 100 mile finishes.
A last runner standing backyard ultra on private farmland in Winchendon with a 4.1666 mile loop. The event also offers 6 hour, 12 hour and 24 hour timed options plus a standalone fastest lap competition.
May 2027
A trail running event on the Wapack Trail in Ashburnham Massachusetts with 21.5 mile, 43 mile, and 50 mile options across rocky, technical terrain with aid stations, drop bag support, and a manual timing system.