As New York City expanded northward, the Flatiron District enjoyed its moment in the late 19th century. As you wander its streets, cast-iron buildings are reminders of that period, when, thanks to an abundance of department stores, it became one of the country's premier retail rows. The area suffered a setback after World War I, and many stores moved even farther north. Later in the 20th century, it would be known as the Toy District and also the Photo District, thanks to the small factories and later photo studios that proliferated there. Eventually, the area's beautiful, historic structures and loft spaces were repurposed and restored, catalyzing the current renaissance. The adoption of the Flatiron District name in the 1980s reflected its changing character as it returned to its retail roots, though now as a popular place to live as well.

The dining scene in the Flatiron District is as varied as any in Manhattan. It includes the celebrated Eleven Madison Park, extra-haute Cosme, and stalwart Il Mulino. Straddling the worlds of shopping and dining, the Eataly at 23rd and Fifth is one of the neighborhood’s newer draws, as is the Shake Shack across the street, in Madison Square Park. Fifth Avenue between 14th and 23rd has emerged as a major shopping area, with locations of Anthropologie, Club Monaco, Kate Spade, Nike, and others. The six-story ABC Carpet & Home is the main anchor of the Flatiron stretch of Broadway, while Sixth Avenue has some very good places to spend your money too.