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