Grand Hotel, ca. 1914.

An iconic example of French Second Empire architecture, the Grand Hotel was constructed in 1868. Designed by Henry Engelbert, the large white marble hotel with its soaring mansard roof was one of several luxury hotels that opened near Madison Square Park after the Civil War. The movement of hotels, theatres, and department store from lower Manhattan into this previously residential area, signaled the beginning of its history as a glitzy entertainment and shopping district (with a bit of seedy nightlife thriving in the area as well, earning it the name Tenderloin).

In the late 19th century, when the theatre district moved further uptown, the Grand Hotel suffered from the loss of those patrons. In the 20th century it was surrounded by the garment district and became a second-rate residential hotel. Today most of the theatres and hotels built in the decade after the Civil War are long done. The Grand Hotel and its somewhat more ornate contemporary, Gilsey House (two blocks north), remain as a testament to that era.