We know where that spot is in Massachusetts, and it's among the top five coolest neighborhoods in America. Within the top 39 that were picked, the particular spot in Massachusetts that ranks among those snagged the #4 overall ranking among the coolest neighborhoods in America. What Massachusetts Spot is Ranked Among the Top Five Coolest Neighborhoods in America? While Boston is Massachusetts biggest city, which has quite a large number of amazing neighborhoods throughout it, there was one that stand out which earned the spot among the top five coolest neighborhoods in America. But it's absolutely beyond impressive to have a particular area be called one of the coolest neighborhoods in America.