Pittsfield has 2 scenic drives trails. These trails range from 0 to 132 miles in length. The most popular trails are Mount Greylock - Massachusetts Highpoint and Berkshire Hills Scenic Drive. Trails.com member Aditya R. recently completed Berkshire Hills Scenic Drive. See all Pittsfield trails.
Mount Greylock - Massachusetts Highpoint
Highpoint rank by height: 31st. As you drive up Mt. Greylock, watch for (and yield to) hikers making their way up and over ...
Berkshire Hills Scenic Drive
A 132-mile loop drive through the scenic Berkshire Hills in western Massachusetts. Every New England landscape is found here—thick ...