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Trail Running in Massachusetts

Massachusetts has 6 upcoming trail-running races scheduled for 2026: 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, The Baystate Dirty Dog Trail Run-Ruck-Walk 5k in Berkley on October 25, Powisset Farm Trail Run - Fall in Dover on October 25, Upton 10.5K and Half Marathon Trail Race in Upton on November 8, and Tortoise and the Hare Trail Races in Salisbury on March 27.

Showing all 6

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
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
Powisset Farm Trail Run - Fall
Trail Running

Powisset Farm Trail Run - Fall

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

Upton 10.5K and Half Marathon Trail Race

November 8, 2026
Upton, MA
Tortoise and the Hare Trail Races
Trail Running

Tortoise and the Hare Trail Races

March 27, 2027
Salisbury, 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.