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Trail Running in Massachusetts

Massachusetts has 6 upcoming trail-running races scheduled for 2026: TVFR Woodland Trail Series in Uxbridge on June 25, Greenbelt's Vineyard Hill Trail Run in South Hamilton on August 22, Houghton's Pond Trail Races (7 Miles and 3.7 Miles) in Milton on October 4, Powisset Farm Trail Run - Fall in Dover on October 25, The Baystate Dirty Dog Trail Run-Ruck-Walk 5k in Berkley on October 25, and Upton 10.5K and Half Marathon Trail Race in Upton on November 8.

Showing all 6

TVFR Woodland Trail Series
Trail Running

TVFR Woodland Trail Series

June 25, 2026
Uxbridge, MA
Greenbelt's Vineyard Hill Trail Run
Trail Running

Greenbelt's Vineyard Hill Trail Run

August 22, 2026
South Hamilton, MA
Houghton's Pond Trail Races (7 Miles and 3.7 Miles)
Trail Running

Houghton's Pond Trail Races (7 Miles and 3.7 Miles)

October 4, 2026
Milton, MA
Powisset Farm Trail Run - Fall
Trail Running

Powisset Farm Trail Run - Fall

October 25, 2026
Dover, MA
The Baystate Dirty Dog Trail Run-Ruck-Walk 5k
Trail Running

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k

October 25, 2026
Berkley, MA
Upton 10.5K and Half Marathon Trail Race
Trail Running

Upton 10.5K and Half Marathon Trail Race

November 8, 2026
Upton, MA

Frequently asked questions

What is trail running?
Trail running takes place on unpaved surfaces like dirt paths, mountain trails, and forest roads. Distances range from 5K to 100+ miles. Trail running emphasizes scenery, elevation, and technical terrain over pace.
What shoes do I need for trail running?
Trail running shoes have aggressive lugs for traction, rock plates for protection, and a more durable outsole than road shoes. Popular brands include Hoka, Salomon, and Altra. Choose shoes based on your local terrain.
How is trail running different from road running?
Trail running involves more elevation change, uneven footing, and slower paces than road running. Expect to run 20-40% slower on trails compared to roads. The focus shifts from pace per mile to effort and time on feet.
What are the best trail running destinations in the US?
Colorado, California, Oregon, and Utah offer world-class trail running. Iconic areas include the Sierra Nevada, Rocky Mountains, Pacific Northwest forests, and Appalachian trails. Browse trail events by state on RACE.