Pittsfield has 2 road biking trails. These trails range from 33 to 52.1 miles in length. The most popular trail is New York Border Cruise Ride and Mount Greylock Challenge Ride.
Mount Greylock Challenge RideView Trail Details
Climb it because it is there. When you summit Mount Greylock, you will be reaching the highest point in all of Massachusetts, where you can enjoy ...
New York Border Cruise RideView Trail Details
Soak up the great scenery of West Stockbridge’s historic commercial Main Street, which is made up of a wonderful collection of early nineteenth-century ...