10 Most Iconic New York Buildings

This post is a self-guided tour of NYC’s 10 most popular skyscrapers.  Come and take a walk with us as we explore 10 famous New York City skyscrapers, old and modern, tall and taller. We’ll start in Lower Manhattan and proceed up north towards Midtown.  Here is a link to the map if you would like to follow along.  Some of these skyscrapers have observation decks.  Find out which observation deck in New York is best

NOTE: This failing post includes just one building named Trump Tower.  Before President Donald J. Trump tweets about how overrated this self-guided tour is, we hope that he is aware that we have a separate post on the more famous 5th Ave. Trump Tower as well as a self-guided tour of NYC buildings erected by the Donald, the world’s smartest and most prolific developer, who has only build the most beautiful structures the world has ever seen. 



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Tip: Entry to both the Empire State Building and Top of the Rock are included for free with the City Pass and New York Pass.  Read our tourist discount pass comparison post.


40 Wall Street (1930) – A

New York Wall Street 40 nycThis 71 floor tower, also known as the Trump Building, was originally called the Bank of Manhattan Building.   At 927 feet (283 m), it is the 123rd tallest building in the world, 25th in the United States, 10th tallest in New York City, and for just a few days, tallest in the world. The Woolworth Building had held the title of world’s tallest building since 1913 and the race was on between the Woolworth and Chrysler Buildings to see which would be crowned the new height champ of all buildings. The Woolworth Building opened in April, 1930, as the new champ of skyscrapers, but four days later, the Chrysler developers ordered the spire, which had been concealed in the air shaft, to be pushed upward, making the Chrysler building the tallest. But not for long. The Empire State Building opened nine months later and was the world’s tallest until 1972.  Our Lower Manhattan Visit New York Tour gets you right in front of 40 Wall Street. Donald Trump’s The Apprentice is filmed here.  Read our full post on buildings related to Donald J. Trump.


One World Trade Center (2014) – B

New York World trade center 1Originally called the Freedom Tower, (there was a controversy over the naming rights) is standing at 1,776 ft. (honoring the Declaration of Independence). It is the tallest building in the Western Hemisphere and 6th tallest in the world. Much of the space has been rented and the top area will be open as a tourist attraction this year! Be sure to check out our Lower Manhattan tours where you are guided through the powerfully evocative ‘Reflecting Absence’, two  stunning memorial pools dedicated to the Twin Towers and the 9/11 tragedy.




Gehry New York (2011) – C

Gehry New YorkThis is Los Angeles’ architect Frank Gehry’s first skyscraper. Officially called Eight Spruce Street, it is the tallest all-residential building in North America. This gleaming 76 story tower, “clad in a rumpled stainless-steel skin”, according to a review in the NY Times, has just about 900 units, all for rent (very unusual for a high rise in NYC to be all residential). It ranks as the 170th tallest in the world, 31st in the United States, and 12th in New York City. The tower stands on a six story public elementary school.


Woolworth Building (1913) – D

New York Woolworth buildingSeen frequently in movies, it was the tallest building in the world from 1913-1930. Designed by Cass Gilbert, super-starchitect of the day, this neo-Gothic beauty, with its 57 floors and 34 elevators, rises to 792 ft. and  is currently the 53rd tallest in the United States, and 20th tallest in New York City. A central figure in the great skyscraper race of the early 20th Century, it was dubbed the “Cathedral of Commerce.” It had an observation deck until 1941 as well as high speed elevators, which were state of the art at the time. It was sold by the Woolworth Company in 1998 for $155 million. A significant portion of the tenants are residents. The price to live there? You guessed right: High.  You could also take a tour of the Woolworth Building.



The Flatiron Building (1902) – E

New York Flatiron buildingStanding at 285 ft. (86.9 m), this 21 floor icon is located on a triangular shaped area, bounded by Fifth Avenue, Broadway, as well as East 22nd and 23rd Street.  By 1892, New York City’s building regulations   no longer required the use of masonry for fireproofing. Thus, began the use of the steel-skeleton design; JP. Morgan’s American Bridge Company in Pennsylvania supplied the steel. The Flatiron Building is called ‘Flatiron’ because it looks like a flat cast-iron clothing iron! Though it was the largest of its kind, it was not the first. Before the Flatiron, other triangular shaped buildings such The Maryland Inn (1782), the Gooderham Building in Toronto (1892) and the English-American Building in Atlanta (1897) were erected. The surrounding area is known as the Flatiron District, named after the building, of course.  Read more about the area on our self-guided tour of the Flatiron District.


Metropolitan Life Tower (1909) – F

New York NY Metropolitan Life TowerNot to be confused with the MetLife Building at Grand Central Terminal, the MetLife Tower faces Madison Square Park, a 6.2-acre public park in Manhattan, located at the intersection of 5th Avenue and Broadway at 23rd Street.  The tower stands at 700 ft. (213.4 m) and has 50 floors. Inspired by the Campanile in Venice, Italy, it is the 135th tallest in the United States and 42nd in New York City. This landmark structure features clocks on all four sides of its tower. Each clock face has a diameter of about 27 ft. (8 m); each number is four feet (1.2 m) tall. In 2002, a state-of-the-art night lighting system, very similar to the one in the Empire State Building, was added.  The colors of the lights alternate in accordance with important events and holidays. The gleaming dome at the top signifies “eternal light” and shines even after the rest of the building goes dark for the night.  


New York Life Building (1928) – G

NYC New York Life BuildingThis 33 story Cass Gilbert classic, the last of his great skyscrapers, is in the Gothic Revival tradition and stands at 615 ft. (187.5 m). The headquarters for the New York Life Insurance Company is housed here.  It is the 269th tallest building in North America and the 89th tallest in New York City. The gold pyramid at the pinnacle consists of 25,000 gold-leaf tiles! For more about Cass Gilbert click here.

Something interesting about Madison Square Park: The world famous sports arena, Madison Square Garden, currently located at 34th Street and 7th Avenue,  was located just northeast of the park from (1878-1925). Famous architect, Stanford White, was murdered on its rooftop garden in 1906 and in 1842, one of the first professional baseball teams, the New York Knickerbockers, played here.


Empire State Building (1931) – H

Empire state buildingProbably the most famous skyscraper in the world, this one and only art-Deco tower is called one of the Seven Wonders of the Modern World by the American Society of Civil Engineers. It was the tallest building in the world from 1931-1970 and is currently the 22nd tallest building in the world, 4th tallest in the United States, and 2nd tallest in New York City. At a magnificent 103 stories, it stands at a total of 1,454 feet (443 m), including the antenna spire, with a roof height of 1,250 feet (380 m). This is the building King Kong scaled in both the classic 1933 film as well as the 2005 remake.  Post 9/11,  the Empire State Building was once again the tallest building in New York, until One World Trade Center exceeded it in 2012.  The Empire State Building underwent a $550 million  renovation in 2010, including over $100 million to make it more energy efficient (something it badly needed); it  was awarded a gold Leadership in Energy and Environmental Design (LEED) rating in September 2011  and is now the highest LEED certified building in the United States.


The Chrysler Building (1930) – I

New York Chrysler buildingThis Art Deco beauty, at 405 Lexington Avenue, rises to 1,046 ft. (318.9 m), and truly is one of New York City’s greatest sites.  The 55th tallest building in the world, 8th tallest in the United States, and 4th tallest in New York City, it has 77 floors and 32 elevators (made by the famous Otis Elevator Company). Though the Chrysler Building had an observation deck until 1945, the top is no longer open to the public. But the lobby, which features a gorgeous mural on the ceiling and the first digital clock, is a must-see. In 1930, this iconic skyscraper outdid 40 Wall Street for the world’s tallest building when its developers pushed the spire through the airshaft.  However, the Empire State Building surpassed the Chrysler Building as the world’s tallest skyscraper, just 11 months later.


30 Rockefeller Center (1933) – J

New York Rockefeller Center sOfficially named the GE Building and also known as the RCA Building, this sky high edifice features an observation deck (Top of the Rock) with spectacular panoramic views. Rising to a mere 850 ft. (259.1 m), this tower has 70 floors and 60 elevators. 30 Rock is the 39th tallest building in the United States and 14th tallest in New York City. It is part of John D, Rockefeller’s Rockefeller Center, which was built in the 1930’s.  30 Rock has been home to NBC Studios since 1933 and its lobby once featured Diego Rivera’s controversial mural “Man at the Crossroads.” Click here to see why this is a choice view of millions.


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