With Massachusetts having such a wealth of history, it also happens to be home to some of the oldest cities and towns in the country. Therefore, it only makes sense that it’s also home to some of the absolute oldest establishments in the history of the country, too, right? Like, for example, some of the oldest bars in America are right here in the Bay State. As it turns out, Massachusetts is home to three of the absolute oldest bars in America! In fact, each of these three establishments are about as old as America.