Flatiron District

The Flatiron District—anchored by Madison Square Park to the north and Union Square to the south—is one of the city's busiest neighborhoods, particularly along 5th Avenue and Park Avenue South. Once known as Ladies' Mile because of the fashionable row of department stores where women routinely shopped, the area is still a favorite for lady-spotting because of the number of modeling agencies and photography studios here. Lovely Madison Square Park, a pleasant green space hemmed in by some of the neighborhood's most notable architecture—from the triangular Flatiron Building to the dazzling, gold-pyramid-topped New York Life Insurance Building to the Metropolitan Life Insurance Tower with its elegant clock face—is the best place to savor the view. Sit and admire the scene with a burger and shake from the park's always-busy Shake Shack, or takeout from the mother (or "mamma mia") of all Italian markets, Eataly, across the street from the west side of the park.