There's a lot of reasons why New England is such a sought out destination for vacationers and tourists alike. And with such a rich history, as well as so many pleasing aesthetics, Massachusetts is at the heart of all those potential destinations. And it's not just the big cities in the Bay State that people are flocking to either. There are definitely a plethora of small towns that have a certain look about them that make for quite the picturesque destination. In fact, Massachusetts is where you can find five of the most picturesque small towns in America.