Call it whatever you’d like: antique, vintage, or historic. If one thing is for certain, the Village is really, really old. Old by New York City standards, and even old by American standards. But which building is the oldest of the old? On this walk, we'll guide you through the Village and show you some of the contenders.

Herring Building, May 4, 1927. Built in 1849 for Silas Clark Herring, the building served as the headquarters of the Herring Lock and Safe Company. The metal "Salamander" safes sold by this company included innovative plaster-of-Paris lining technology, which purported to be fireproof. The neo-Grec, though more generally vernacular building, is five stories tall and is given its odd shape by the meeting of Ninth Avenue and Hudson Street at 14th Street. The northern section of the building, which gives it the shape that earned the moniker of "Little Flatiron" was actually an addition circa 1860. In the late 19th and early 20th century the building was home to variety of food related businesses, including grocers, saloons, restaurants, and at least one butcher. This address has been best known in the late 20th century, as the location of a series of well-known clubs, the most prominent being the basement BDSM Hellfire Club (1971-2002).

One of New York’s most beloved and iconic landmarks, the Flatiron Building is known for (among other things) its unique shape. But of course, the corner of 23rd Street and Fifth Avenue isn’t the only place in Manhattan where streets intersect at quirky angles. In fact, the Village’s off-the-grid streets are full of them. More information can be found here.