The world's tallest building upon completion in 1913 (it was surpassed in height by the Chrysler Building in 1930), Cass Gilbert’s 792ft-tall masterpiece is a neo-Gothic marvel, elegantly clad in masonry and terra-cotta. Entry to the breathtaking lobby is only accessible on pre-booked guided tours, which were on pause as of this writing. Instead, find a seat across the street in City Hall Park and crane your neck toward the sky to eye the 60-story structure's exceptional stonework.
At its dedication, the building was described as a "cathedral of commerce"; though meant as an insult, FW Woolworth, head of the five-and-dime chain-store empire headquartered there, took the comment as a compliment and began throwing the term around himself. Today, it's more like a cathedral of condos, as the top 30 floors have been converted to ultraluxury residences, including a "Pinnacle Penthouse" that takes up the top seven floors and includes an open-air observatory.
