The neighborhood began its slow transformation around the turn of the 20th century, beginning with the construction of The Dakota in 1885. Designed by architect Henry Janeway Hardenbergh, designer of the Plaza Hotel, The Dakota was built in a North German Renaissance style, which can be seen in its deep, sloping roof. It’s often said that The Dakota derived its name from the fact that the Upper West Side was as sparsely populated and remote as the West’s Dakota Territory.

Now a designated historical landmark, the building would unfortunately lapse into infamy when its most famous resident, John Lennon, was gunned down in 1980 in the building’s entryway by a deranged fan .

A few years after the construction of The Dakota the Upper West Side would receive its very first skyscraper in the form of the 17-story Ansonia. Built by William Stokes, a tycoon with a dream, in 1904, the Ansonia was the most opulent building in all of New York City. Boasting a beaux-arts design and a Parisian-style roof, the building had over 300 suites, the world’s largest indoor swimming pool and a ballroom that could accommodate 1,300 dinner guests.

The building’s over-the-top grandeur quickly made it the preferred residence for some of the city’s nouveau riche like baseball players, boxers and even gangsters. Babe Ruth and Jack Dempsey were two well-known residents, and it was in the Ansonia that several members of the Chicago White Sox colluded with gangster Arnold Rothstein to throw the 1919 World Series.

While visitors to NYC today can’t stay in either The Dakota or the Ansonia—unless they have a friend living in the buildings—it’s still a lot of fun to walk around the Upper West Side taking in the buildings’ grand architecture and history. Afterward return back to The MAve boutique hotel in the Flatiron District for a good night’s rest.

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Perhaps the most notable building on the Upper East Side is the Solomon R. Guggenheim Museum. Designed by architect Frank Lloyd Wright, the New York Guggenheim is one of the only museum’s in the world whose exterior is more famous than the collection it houses. Wright’s inverted-circular tower was built in 1959 in a testament to modernism’s unique style and the building has been a massive hit with the public ever since.

Not far from the Guggenheim the Whitney Museum of American Art is housed in the striking Breuer Building. Designed by the Hungarian architect Marcel Breuer, who was trained at the famed German design school Bauhaus, the building was hailed as a somber construction at the time of its completion in 1966. Admiring its gray exterior and inverted-ziggurat shape, it’s easy to appreciate the building’s heavy, almost stoical appearance.

Another museum on the Upper East Side with a fantastic architectural story is the Frick Collection. This museum is housed in the Frick House, which was commissioned by Pittsburgh industrialist Henry Frick in 1912. The house was designed by architect Thomas Hastings, who also designed the grand New York Public Library. The house, with its ample lawns and grand atrium, has the feeling of a country estate despite its central location on Fifth Avenue. Inside the minimalist décor perfectly complements the museum’s collection of European masterpieces.

Currently guests at our boutique hotel The MAve staying for four nights will receive their fifth night free, giving them the extra time to wander the city and take in the small details, like the architectural designs of the Upper East Side.

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