Skyscrapers, Art Deco & Bitter Rivalries: The Landmarks of Midtown East

New York City

  • "Men at Lunch" was photographed on top of Rockefeller Center.
  • The Flat Iron Building, photographed from 24th and 5th.
  • King Kong on top of the Empire State Building.
  • The Rose Main Reading Room.
  • The front of the New York Public Library.
  • Grand Central Terminal.
  • Mercury stands on top of the Grand Central facade.
  • Looking up at the Chrysler Building. Note the giant winged wheels on the 31st floor.
  • The 1st floor lobby with the Chrysler Building painted on the ceiling.
  • The lobby of the Waldorf Astoria.
  • The mosaic domes on the ceiling before the nave.
  • The "Sanctus" rose window.
  • The Tiffany & Co. altar to Saint Michael and Saint Louis.
  • The neo-Gothic nave of St. Patrick's.
  • "Lunch atop a Skyscraper, 1932" was photographed on top of Rockefeller Center by Charles C. Ebbets.
  • Atlas looks at St. Patrick's Cathedral.
  • Afternoon tea at BG Restaurant on the 7th Floor.
  • The Vanderbilt Castle, the largest single family home in an American city.
  • The elegant Palm Court at the Plaza Hotel.
  • The Plaza Hotel.

2 hours and 30 minutes
2.5 mi
Guided by Michael
Michael Williamson


As Manhattan's population boomed at the turn of the 20th century, the island had nowhere to expand but up. Tycoons and dreamers looked to outdo one another while architects and artists gushed at the opportunity to add their marks on the city skyline. Come explore the quintessential neo-classical buildings of Midtown East and the stories behind them.

About Your Guide

Kansas born, Ohio raised, New Jersey schooled, and now: New York native. I devour history and non-fiction books, especially anything about Nieuw Amsterdam, Gotham, The Five Boroughs and the Empire City. My dog and I endure four flights of stairs to reach our Upper West Side apartment, but wouldn't change a thing.

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Guide Points

  1. Flatiron Building

    In a city bursting with iconic architecture, the Flatiron Building is one of the most photographed in Manhattan. The unusual triangular we…

  2. Empire State Building

    Nearly thirty years after the Flatiron Building was completed, a competition erupted between the heads of General Motors and Chrysler to se…

  3. New York Public Library

    If you searched for an architectural metaphor that celebrated the importance of education, it would be difficult to find something more fit…

  4. Grand Central Terminal

    The exterior of the Beaux-Arts transportation hub is best viewed from the intersection of 42nd St and Park Ave. From bottom to top, the la…

  5. The Chrysler Building

    While the Empire State Building won the competition for height, the Chrysler Building certainly won for Art Deco styling and for being the …

  6. Waldorf Astoria

    For over 150 years, the Waldorf Astoria Hotel has been synonymous with luxury, opulence, prestige and service. The 47-story Art Deco insti…

  7. St. Bartholomew's Church

    And now for something new and completely different. This Episcopalian Church was built in 1917 in a Byzantine Revival style, as evidenced …

  8. St. Patrick's Cathedral

    The sharp, 330-foot tall twin spires, sharp pointed arches, and ornate stone carvings on St. Patrick's Cathedral are textbook neo-Gothic ar…

  9. Rockefeller Center

    In 1928, Rockefeller leased the plot of land from Columbia University in order to form a consortium to build a new home for the Metropolita…

  10. Bergdorf Goodman

    Bergdorf Goodman is a luxury goods department store that is unique for its choice to keep its global footprint limited to 5th Avenue betwee…

  11. The Plaza Hotel

    Our walk of important institutions of Midtown ends at The Plaza Hotel, the first of two hotels in the city crowned with National Historic L…

Sidewalk Reviews

  1. 2 Reviews

    1. Reyna Claps

    Dec 26, 2019

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