history.

Long before the Flatiron building cast its shadow over Broadway and lent its name to the eponymous neighborhood, the section of Manhattan spanning about 38 blocks from 18th to 28th Street between Sixth and Lexington avenues was already a central part of New York City. During the War of 1812, the Madison Arsenal, named for President James Madison, sat at the heart of the neighborhood. Thirty years later, Madison Square Park was built in its place.

After the Civil War, the American elite flocked to the area because of its proximity to Wall Street and distance from the filth of the Seaport. The Park was quickly surrounded by businesses and brownstones. Hotels settled in, among them the prestigious Fifth Avenue Hotel. Today, these hotels, where Boss Tweed and Jay Gould once smoked cigars and cut deals, have been replaced by office buildings.

At the turn of the 20th century, department stores began popping up along Sixth Avenue to cater to well-heeled society women. Later known as the Ladies Mile, the stretch between 14th and 24th streets included retail meccas Lord & Taylor and Bergdorf Goodman.

The area also became an artistic and literary hotbed. At 14 W. 23rd St., Edith Wharton found inspiration for her novels in the lives of her wealthy neighbors. Herman Melville of Moby Dick fame called 104 E. 26th St. home. The neighborhood also housed a glut of theatres, including the Booth Theatre and the first and second Madison Square Gardens. Many of these still operate today. The theatres brought with them plenty of drama – both on and off the stage. The architect Stanford White, who designed the Washington Square Arch, maintained a love nest on 24th Street for his infamous trysts with the beautiful young actress Evelyn Nesbit.

But as the city continued its inevitable march north, the wealthy residents followed and for a while the district was largely commercial. In the mid-20th century, it was known as the Photo District as studios moved into the large, airy lofts. During the late 1990s, it was dubbed Silicon Alley for the influx of Internet and new media companies. Fashionable stores, clubs and restaurants – key attractions of the area today – followed the hordes of young professionals, and rising rents began to push small businesses out.

Around 1985, real-estate agents needed an attractive advertising name for the increasingly popular neighborhood, so they crowned the area the Flatiron district, after the iconic 1902 building that sits on the island where Broadway and Fifth Avenue meet. The district is now home to about 10,000 residents; about 60 percent live in non-family households. It is hard to believe that in 1928, the Metropolitan Life North Building was capped at 36 stories high, instead of the planned 100, because the owners didn’t think they could ever rent out that much space.

But even as the Flatiron district undergoes constant change, traces of its history still remain. The Gramercy Theater, once an old art house on 23rd Street, is now a popular concert venue. Along Sixth Avenue, young women wander thriving sections of the old Ladies Mile where they can now find stores like Nine West, Gap, and Sephora. The old photographers’ lofts are now occupied by hip public relations and advertising firms

As I walk under the shadow of the Flatiron, I try to imagine a time when skyscrapers were so rare that the Flatiron could be seen from Central Park. And as I cross the street, I can’t help but think: it must have been a lot safer to jaywalk in the days when hansom cabs, not taxi cabs, made their way up the enduring asphalt of Broadway.