Another plus of Madison Avenue is it runs through the heart of the Upper East Side, New York's most exclusive, and prettiest, residential neighborhood. To clarify, Fifth Avenue is very much an Upper East Side avenue as well, but the shopping part of it is further south, in Midtown. The avenues have the grand prewar apartment buildings that house New York's most famous high society families, but the cross streets in the sixties, seventies and eighties contain beautiful townhouses and are much prettier in my opinion.