10 Sheridan Square, steel framing, March 6, 1929.

10 Sheridan Square, under construction, April 8, 1929. The 14-story apartment house called the Shenandoah loomed over its more low-rise neighbors when constructed in 1929. It remains still one of the taller buildings in the area, directly across from a pocket park on one side and a small garden on the other. Designed by famed apartment house and hotel architect Emery Roth, the simplified neo-Romanesque building includes a multi-colored stonework base with large segmental-arched windows. The tower, with arched loggia (open portico) can been seen in both construction photographs set back from the corner on the Sheridan Square-facing facade (on the right in the photographs). Take note of the small stone and metal sea creatures, elephants, and dragons that decorate the ground floor, which has been occupied by a gay bar called Monster since the 1970s.

“The Shenandoah”/10 Sheridan Square/80 Grove Street This building was also originally an apartment hotel, albeit presumably intended for more middle-class residents than the intended tenants of 24 Fifth Avenue. It was built in 1928-29 and designed in what the Greenwich Village Historic District designation report refers to as “a severely simple version of Neo-Romanesque” style. The battlements, use of irregular and multi-colored stone and dark brick lend to a medieval feel to the exterior of the building. The living units were designed predominantly as one-room apartments which served as living, dining and sleeping space, with a bathroom and a pantry directly adjacent.

Greenwich Village Inn, 1933. The origins of the Greenwich Village Inn date to before the First World War when Polly Holliday ran a restaurant that became a gathering spot for Greenwich Village radicals and bohemians. In 1916 she moved her establishment to 5 Sheridan Square. She also took on a new partner, Barney Gallant, an early nightclub entrepreneur. Though the original venue had been full of tried and true Village bohemians, this new spot, with Gallant's marketing, became more of a place where outsiders came to see the bohemians. Soon the place was flooded with flappers, undergrads, and tourists. Gallant made a name for himself—and become a bit of a local hero— when in 1933 a few of his Greenwich Village Inn waiters were arrested for Prohibition violations. Gallant offered himself up in their place and served 30 days in the notorious Tombs. By the 1940s the venue had suffered in reputation and popularity. According to a 1971 book, the Inn was largely a mafia front in its final years. Closed in 1951 the building was taken over by the newly founded Circle in the Square theater and was demolished for a 17-story apartment house in the late 1950s.

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.

"When Prohibition was introduced, I hoped that it would be widely supported by public opinion... I have slowly and reluctantly come to believe that this has not been the result. Instead, drinking has generally increased; the speakeasy has replaced the saloon; a vast army of lawbreakers has appeared; many of our best citizens have openly ignored Prohibition." –– John D. Rockefeller