Boston's been around a while, which means people have been drinking in Boston for a while, which means there are a bunch of amazing old bars that remarkably haven't been destroyed in the aftermath of an uncountable number of crushing sporting defeats.
While it may not be the oldest bar in the city (established in 1890), Amrheins is home to the oldest hand-carved bar in all of America as well, as the first draft beer pump in Boston (they probably thought it was just a fad).
Founded in 1868, this German-American restaurant is one of the oldest in the city (okay, the second oldest). Just across the street from it's original location, the spot landed itself in the National Register of Historic Places in 1980.
The Town Crier's job was to shout the big news across town, and the original proprietor of the Bell in Hand shouted about the Boston Tea Party, the Declaration of Independence, the impending Battle of Bunker Hill, and of course, the defeat of the British.