Flatiron District

The Flatiron District—anchored by Madison Square Park on the north and Union Square to the south—is one of the city's busiest neighborhoods, particularly along 5th Avenue and Park Avenue South. In some ways it should still be called Ladies' Mile: the area is a favorite for spotting models because of the number of agencies and photography studios here. Lovely Madison Square Park, a pleasant green space hemmed in by the neighborhood's notable architecture—from the triangular Flatiron to the dazzling, gold-pyramid-topped New York Life Building and the Metropolitan Life 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 new foodie favorite, Eataly, across the street from the west side of the park.