3. Madison Square

Chester A Arthur Statue Madison Square Park at 23rd and Broadway

Madison Square was named after the Madison Cottage, a tavern and popular travel stop along Broadway, and probably after President James Madison. Originally used as a regimental training ground, it has since become associated with famous buildings: the original Madison Square Gardens, the MetLife building (now home to the swanky New York Edition hotel), and at the southeast corner and arguably the city’s most unusual building and the first skyscraper built in Manhattan, the Flatiron Building.