PARK AVENUE

Let’s be honest. Fifth Avenue along Central Park is more posh, and it’s got its own playground right across the street. But Park Avenue is wider, and at least has token greenery–those grassy traffic islands that line the middle of street. It’s also got its own underground railroad line–built in the 19th century as an open cut that connected Grand Central Station to the rest of the country. Beginning in the 1890s, after the cut was filled in, this entire stretch of street from the Sixties to 96th joined Madison and Fifth Avenues as Manhattan’s Gold Coast–home to wealthy industrialists. By the 1920s, many of the grand mansions built on Park gave way to immense, fortress-like apartment buildings, designed in a dizzying variety of styles–Romanesque, Georgian, Italian Renaissance, Art Deco–sometimes all in the same structure, invariably guarded by a doorman. Park Avenue even has its own brick fortress: the 7th Regiment Army. The oldest money in the New World, and some of the newest too, lives on this street.