Manhattan Architecture Walking Tour (Self Guided), New York

The skyscraper, which has shaped Manhattan's distinctive skyline, has been closely associated with New York City’s identity since the end of the 19th century. Despite the Great Depression, some of the world’s tallest skyscrapers were completed in Manhattan during the 1930s, including numerous Art Deco masterpieces that are still part of the city's skyline – most notably the Empire State Building, the Chrysler Building and the 30 Rockefeller Plaza that forms the centerpiece of Rockefeller Center. Even now that other commercial structures have reached far greater heights, they remain icons that refuse to relinquish their special meaning.

As you will also see on this special tour, however, Manhattan’s intricate architecture is not represented only by the huge number of tall buildings. Proper handling of the large-scale planning and technical aspects allowed the Grand Central Terminal complex to be seen easily from below. And now, even with high-rise buildings around, it stands as a solid and radiating icon of innovative urban design. The station’s main facade, a Roman triumphal arch, symbolizes the gateway to the city.

Not far from the Empire State Building, Macy’s original flagship store is 9 stories above ground and covers an entire block. A department store in the GRANDEST tradition, it oozes with history from an architectural standpoint. Make sure you see the old wooden escalators on the Broadway side!

Yet another unique and majestic sight, the Flatiron Building stands at Broadway and Fifth Avenue – the two most important streets of NYC. Although you cannot visit inside, the main attraction is outside where the wedge shape captivates tourists flocking around the park opposite taking photo after photo. Besides its subtle elegance, the building has an interesting backstory, too. Due to the wind-tunnel effect at the site, in the early 20th century, men would hang out on the corner and watch the wind blowing women’s dresses up so that they could catch a little bit of ankle. This entered into popular culture and there are hundreds of postcards and illustrations of women with their dresses blowing up in front of the Flatiron Building.

Follow our self-guided walking tour to visit some of the most famous architectures in Midtown Manhattan at your own pace.