No matter where you go in the Berkshires, more often than not, it seems like you will end up in a town that is at least relatively aesthetically pleasing. Several cities and towns in Massachusetts are known for having a pretty great look to them. This stems from the incredibly rich history that the Bay State has. But it just so happens that two towns within the Berkshires were recently named as some of the 'Most Picturesque Towns in Massachusetts'.