As one of the most important cities in the world, New York City has forged a legacy that transcends the notion of just being a popular American city to become a symbol of power, money, freedom, and history.
That symbolism is often captured in a quasi-permanent state through its architecture, which, without words, can tell us the story behind the moment in time when they were conceived.
Naturally, in its almost 400 years of history, the city has evolved its architectural language as a reflection of its ever-changing needs and its reciprocal influence with the world.
While there are plenty of architectural icons spread across the city, the buildings listed here were, in a way, an influential force that shaped the urban landscape that now makes New York City.
The Military Genesis of New York City
Probably one of the oldest buildings with significant historical importance in the development of the city, and the United States as we know it, is Castle Clinton.
Built on a small artificial island in 1811, this circular sandstone fort defended what was then the Dutch settlement of New Amsterdam.
Today, due to landfill, it sits in the middle of The Battery (Battery Park). From 1855 to 1890, Castle Clinton became the world’s first immigrant depot, receiving over eight million immigrants, decades before Ellis Island and the iconic Statue of Liberty were built.
Not too far from Battery Park is Federal Hall, one of the best Greek Revival-style buildings in the city. While the current structure dates to 1842, the original building dating back to 1703, served as New York’s first City Hall.
This original building served as the meeting place for the colonial Stamp Act Congress to draft its message to King George III claiming entitlement to the same rights as the residents of Britain and protesting “taxation without representation,” leading to the American Revolution.
After the Revolution in 1785, the building served as the meeting place for the Congress of the Confederation, the nation’s first central government under the Articles of Confederation.
But once the United States federal government was established in 1789, it was renamed Federal Hall, serving as the home to the first Congress, Supreme Court, and Executive Branch offices.
But most importantly, it was here where George Washington took the oath of office as the first President of the United States.
The original building was demolished in 1812.
A Mercantile Development of the Island of Manhattan
The southern tip of Manhattan, especially its harbor, was key to the creation of New York City. The free-flowing waters of the port of New York served as the spark that ignited the development of the modern city we know today.
One of the first architectural side-effects of the port came in 1899 when an increased volume of trade required the construction of a bigger Customs House (now the National Museum of the American Indian).
This Beaux-Arts building was designed with decorative classical architectural details and elaborate sculptures that rivaled Classical buildings in Europe.
It symbolized the wealth, power, and international status of the United States as it grew as one of the top mercantile and political powers in the world.
Commerce proliferated in what was now the premier port of the United States, and with it, lower Manhattan grew from old counting houses to taller buildings.
Broadway, initially a path used by Native Americans and later by Dutch traders to connect New Amsterdam with Albany, was widened from a street wide enough for wagons and stagecoaches to a fashionable residential street for the wealthy.
Similar to the Roman insula 2,000 years ago, the rich inhabited the desirable lower levels. At the same time, the poorer lived on the upper floors – a concept we’ve now inverted thanks to the elevator’s invention and, with it, the introduction of the “penthouse.”
But as commerce invaded Broadway, it pushed the city’s affluent mercantile population northward, leaving this famous avenue as the city’s primary business thoroughfare.
This scene repeated itself for the next century, expanding and redeveloping the city one neighborhood at a time.
For those who couldn’t afford to move north, the recently built Brooklyn Bridge now gave access to the less developed Borough of Brooklyn.
After its completion in 1883, the Brooklyn Bridge became the longest suspension bridge in the world at the time. It was also an architectural and engineering marvel that added to the magnificent scale the city was aiming for.
And just three years later, a gift from France would pop up down on Liberty Island to become another New York icon: The Statue of Liberty.
Growing North: The New York City Grid and the City Beautiful Movement
The city’s growth northward and Broadway’s popularity put economic pressure on the property owners in neighborhoods like Soho.
Slowly, the beautiful brick row houses gave way to commercial properties, with many of them introducing a new façade style made of cast iron panels bolted to the brick wall.
These new cast-iron facades distinguished the neighborhood as a high-end area, which quickly became the heart of the shopping district.
While Soho’s shopping district’s importance has changed throughout its history, its architectural significance has been cemented as being the world’s largest remaining cast-iron district.
The city’s growth followed a street grid masterplan laid out in 1811 when it was mostly an imaginary construct.
At that time, the city’s Commissioner’s Plan envisioned the city growing to what is Washington Heights today, surveying 12 avenues and 155 cross streets, starting from Greenwich Village.
The Commissioner’s Plan of 1811 is considered “the single most important document in New York City’s development.” Still, the original plan lacked the kind of parks that graced cities such as London and Paris.
To address this, the most significant alteration to the original plan was introduced in 1953 with the creation of an 843-acre open area that would later become the now-iconic Central Park, built between 1857 and 1876.
As New York City kept expanding and growing as a new commercial and cultural capital, the city looked forward to cementing its status with a few majestic landmarks, including Grand Central Terminal in Midtown Manhattan.
Opened in 1913, the terminal was built on the site of two similarly-named predecessor stations, the first of which dates to 1871.
Influenced by the vibrant City Beautiful movement of the late 19th and early 20th century, the Beaux-Art design behind the new Grand Central Terminal satisfied the desire to invigorate midtown Manhattan and transform regional transportation.
The majestic vaulted main concourse and the beautifully decorated facade would become the gateway to New York City.
The station looked and functioned like no other, merging elegance with efficiency. This terminal’s exuberance showed visitors that New York City and its railroads weren’t shy at all.
Books weren’t shy either after the completion of the New York Public Library building in 1911. It followed the similar monumental Beaux-Arts style that characterized every major building shaping the city in this era.
Just eight blocks north, the Roman Catholic Archdiocese of New York had recently set its new seat with its St. Patrick’s Cathedral, erected in 1879. This decorated neo-gothic cathedral is one of those buildings you can’t miss seeing when in New York City.
But not every neighborhood fared equally. As business in New York City grew, so did the population.
By the end of the 19th century, the Lower East Side was the densest area in the world, with living conditions that left much to desire as mostly the impoverished lived here.
Immigrants crammed in wherever they could and lived with no sunlight, plumbing, sanitation, and barely any space. The slum streets were filled with crime, diseases, trash, and human waste.
His beautiful photo journaling began the conversation between the middle and upper classes that led to significant housing reforms in 1901.
Creating the Framework for Urban Development
By 1916, due to the city’s chaotic, fast-paced and unprecedented development, the city passed the first citywide zoning code in the U.S. to regulate new construction and establish a more harmonious growth of the city.
Both acts formed the framework that defined the architecture and urban fabric of the New York City we know today.
These reforms –along with game-changers like the elevator, electricity, and new materials– sprung other changes in the living and architectural landscape of New York City, forming the basis for developing the high-rise building.
The skyscraper, as we know it, was now being borne.
The Skyscraper Trend
The high-rise trend started in 1884, with apartment buildings like the luxurious Dakota Building on the then sparsely populated Upper West Side.
With only eight stories and a blend of North German Renaissance architecture with French-influenced apartment layouts, the Dakota Building set an example for the middle class to also desire vertical living.
In Downtown, things were changing too. In 1902, the city welcomed one of the most significant structures ever built: The Flatiron Building, designed by Daniel Burnham.
Like never before, the building embraced the site’s acute triangular shape and the developing steel skeleton construction technique of the era.
The result was a narrow 22-story tall structure (285 feet high) that resembles a classical Greek column with a limestone base and a terracotta shaft and capital.
Upon completion, The Flatiron became one of the tallest buildings in the world, but it was received with mixed criticism.
Among them, tenants feared moving into the slender building, thinking it would fall down. A notion of height and slenderness is only enhanced by the perspective created at its narrowest point.
The Flatiron is now considered one of the world’s most iconic skyscrapers and a quintessential symbol of New York City. Its edge, which is almost as sharp as a ship, still amazes people to this day.
Many of New York’s iconic skyscrapers were built during a period of fierce competition among developers in the early 20th century. A period when the title of the “tallest building in the world” was quickly passed from building to building.
The building known as 40 Wall Street (Trump Building), with its distinctive copper roof standing at 927 feet, was once the tallest building in the world when it was completed in 1930, a title it held for only a few weeks.
That same year, Walter Chrysler was already building his now-famous Chrysler Building, which topped 40 Wall Street by 119 feet.
The Chrysler perfectly epitomizes its time with its sleek Art Deco top and sky-piercing spire – an era of industrial power, wealth, and large-scale building.
But Chrysler’s achievement was short-lived, too, as less than a year later, the new Empire State Building reached a total of 1,250 feet after just 14 months of construction.
But this race towards the skies was short-lived as interests shifted into creating a vertical city for all, not just the upper class.
This shift left the Empire State Building as the tallest building in the world for 40 years – the longest any skyscraper has held to that title.
The Effects of WWII in New York’s Architecture
After the end of World War II in 1945, another wave of immigration hit the U.S., and with it, the state-funded mass housing experiment that defined New York City’s architecture for the next two decades bloomed.
But, in a plot twist no one expected, the publicly subsidized high-rise buildings for the working middle class quickly went from being the tool that solved the housing problem of the city to being blamed for it.
By the late 1960s, the urban sprawl became a conflicting phenomenon to vertical building, bringing an end to the high-rise boom as the white middle class fled the downtown in search of a better life in the suburbs.
Several high-rise neighborhoods that once housed the idealized middle class became neglected warehouses for the poor. Buildings fell apart from mismanagement, crime, corruption, and abandonment.
But, this dark high-rise era didn’t last long.
A New High Rise Era
A new high-rise age dawned by the late 1970s when glass towers began to rise from the ground. And with them, another ideology took place.
Now, housing towers were no longer built as a tool for social equity, but instead, they were a financial instrument of market capitalism – the condominium.
An important precursor of this “glass tower” style was the Seagram Building, designed by world-renowned Mies Van der Rohe in 1958.
With its monumental simplicity, which expresses its structural frame and rational use of repeated building elements, this office building epitomizes the introduction of modernist ideals from Europe into the United States.
Two iconic structures that took this “glass tower” rationale were the former World Trade Center twin towers. Even during construction in 1971, they became the tallest structures in the world – reaching up to 1,368 feet.
It’s interesting to note that New York City dominated the tallest building in the world chart from 1908 to 1973, with a total of seven buildings, each surpassing the former.
Still, the city hasn’t regained its “tallest building in the world crown” since the Chicago Sears Tower surpassed the World Trade Center in 1973.
Reinvention: the New York City of the 21st Century
As we reached the end of the 20th century and beginning of the 21st, New York City experienced another shift in architectural attitude to one that tried to incorporate the best aspects of previous phases of its history.
Again, the city pushed towards the sky with slender and glistening glass towers like One57, 432 Park Avenue, and Central Park Tower condominiums –currently the tallest residential building in the world– while it simultaneously pushed for better public open spaces, which are essential to the urban fabric.
The revamping of obsolete industrial revolution structures like the High Line into linear parks and the red TKTS Booth steps in Time Square are two perfect examples of the city grasping its new identity of a metropolis that not only builds upwards but also builds for the public user at street level.
Additionally, as the city grows, so does its need for open spaces and parks, which brings us to the creation of Little Island on the Hudson River.
This artificial island park, sculpted with 132 tulip-shaped structures, creates an organic and intertwining space that provides a new way to enjoy the outdoors in New York City.
These structures created not only new New York City landmarks but also additional interactive public areas where people can enjoy the city in different ways.
Down at the World Trade Center, the city again pushed towards the sky with the current tallest building in New York City – One World Trade Center with 1,776 feet – symbolizing the year when the United States Declaration of Independence was signed.
The World Trade Center also pushed the boundaries with the new monumental WTC Transportation Hub, also known as The Oculus, designed by Santiago Calatrava.
The station, notable for its white steel ribs rising to the sky and its white marble-clad expansive interiors, opened in 2016, and to this date, it is the most expensive train station in the world – costing over $4 billion.
Just next to it is one of the most emblematic memorials in the United States.
The 9/11 memorial immortalized the former towers with its minimalist yet beautiful open park memorial dominated by two sunken pools symbolizing the void created by 9/11 and those who perished.
New York is a city that is continuously reimagining itself, and it is this incredible mix of architecture and layers of history that make it a unique place in the world.
This evolution is not over. New York City is not finished.
For your convenience, below is a map with the location of every building mentioned in this article.
If you’re visiting many of these iconic landmarks and New York City attractions, I highly recommend getting the New York Sightseeing Pass to save money on over 100 attractions.
Additionally, you could visit, learn, and explore more of many of these buildings and New York City landmarks through one or a few of these highly recommended tours.
Essential Info: Logistical Tips and Tricks to Book your Trip
BOOK YOUR FLIGHT
Regarding cheap airfare, I highly recommend using Skyscanner and Expedia. These are two of the sites I use the most due to their exhaustive search on several websites and airlines around the world. They usually bring the cheapest fares.
Additionally, I recommend getting the WayAway Plus membership to save money on cheaper fares and earn cashback (sent straight to your PayPal) on your bookings.
BOOK YOUR ACCOMMODATION
For hotels, guesthouses, apartments, and other types of accommodation, I highly recommend Booking.com. They are my go-to booking site because they usually have the cheapest fares.
If you’re a registered Booking.com user (“Genius”), you can take advantage of their “Genius discount” to save even more money. I almost always book my accommodation with Booking, and I’ve saved thousands of dollars with their Genius discount.
And of course, as one of the largest travel booking sites in the world, Expedia is another excellent accommodation booking site with a free reward program and discounted member prices.
If you’re looking to save money by staying at a hostel, HostelWorld has the largest inventory of hostels with shared dorms and private rooms. On the other hand, Vrbo offers a wide variety of rooms and apartments at affordable prices.
DON’T FORGET YOUR TRAVEL INSURANCE
Travel insurance with comprehensive coverage will protect you against unexpected events like theft, cancellations, injury, and illness.
I use HeyMondo to insure my trips and recommend them. Their affordable plans offer a 24/7 assistance platform for claims, medical coverage for every traveler, adventure sports and covid-19 coverage, and more. And better yet, GloboTreks readers get 5% off their plan! Get a quote.
Alternatively, if you’re a nomad and travel often or long-term, then SafetyWing could help you save a lot of money on long-term travel insurance.
FIND THE BEST TOURS AT THE BEST PRICES
If you’re looking for the best day tours and cheapest ticket entrances to local attractions, I recommend checking Viator, as they have the largest selection of attractions, passes, and activities all around the world.
BOOK YOUR LOCAL TRANSPORTATION AHEAD OF TIME
Bookaway offers the easiest and most accessible way to book overland transportation with local operators, be it by bus, train, ferry, plane, mini-van, or even private transfers.
If renting a car, then I highly recommend DiscoverCars to get the largest car selection at the best price.
OTHER TRAVEL AND MONEY-SAVING TIPS?
Lastly, check out my resources page for some of the best products and companies to use for your trip. If you like saving money (like I do!), then this page will help.
Maps and graphics from Wikipedia. Photos of Castle Clinton, St. Patrick’s, Chrysler, and Dakota from Flickr Creative Commons. Image of the National Museum of the American Indian by David Sundberg for the Smithsonian.
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