• Photo: Marco Rubino / Shutterstock

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. 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 the neighborhood's notable architecture—from the triangular Flatiron to the dazzling, goldpyramid–topped New York Life Building and 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 mother (or "mamma mia") of all Italian markets, Eataly, across the street from the west side of the park.

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