NYC’s Best Architecture Tour Is All on One Subway Line | Walking Tour | Architectural Digest

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Sep 15, 2026 #Architecture
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The New York subway system is very complicated, but I'm going to make it simple for you.
For the best architecture-focused tour of New York, you only need to remember one letter,
the letter F. You can get the biggest range of architecture from one subway line. You can see
great buildings from the 1850s, incredible contemporary architecture, and the history
adds to your understanding of the poetry of architecture in New York.
I had a very sheltered Upper East Side childhood, but one thing I always wanted to do,
and my father promised he would do it, was take me on the subway when I was like four years old.
My mom wanted no part of that. So we made a plan to take the subway out to Coney Island,
and that was the first time I was ever on the subway, and it was a very memorable trip with my
dad. So on our architecture tour of New York via the F train, we're going to take that train
all the way to Coney Island. Are you ready? We just got off the 34th Street stop of the F train,
and I'm in front of Macy's in Herald Square. But what I want to talk to you about is what's
behind me, the Empire State Building. It's one of the great miracles of architecture of the world.
The Waldorf Astoria used to stand on that site at 34th Street and Fifth Avenue.
The opportunity to move it was what inspired a developer called Jacob Raskob to build the tallest
building in the world. It was a very close race for that title at that time. The Chrysler Building
had been the tallest building in the world, and when the Empire State Building was finished in
less than 500 days in 1931, it was the tallest building in the world, and it remained that way
until the World Trade Center at the time. Its top, which is what we all love about it,
was designed to be an airship mooring mast. This is not something that it was ever actually used
for, but in 1930, airship travel was considered the coming thing before the Hindenburg put that
notion to rest, and the Empire State Building needed a distinctive crown. The next big science
fiction thing that the Empire State Building contributed to was King Kong, and where did they
choose to set that in the climactic ending, but on the brand new skyscraper that had caught
everyone's imaginations? The top of the Empire State Building is an example of how the whole
building is sort of about the future and how it inspired thoughts about the future. It still kind
of does, even though it's 100 years old. So we just got off the F train at 23rd Street.
Madison Square is one of the most fascinating intersections of important streets, Fifth Avenue
and Broadway, and also great New York stories. What you can't see on that side of the square
is the ghost of the original Madison Square Garden, where in 1906 the architect Stanford
White was shot, and it was called the murder of the century. What you can't see over here to my
left is the ghost of the Fifth Avenue Hotel, which is where New York society met before eating dinner
at Delmonico's. This is all great New York folklore. Flatiron Building, which is what we're
going to talk about, is itself a great story, the story of a great pioneering skyscraper. 1902,
Chicago architect Daniel Burnham. Flatiron, so-called because it's the shape of an iron,
but more recently someone with a lot of imagination said it's the most New York
building because it looks like a slice of pizza. I mean, it's in the eye of the beholder,
these triangles, you know what I'm saying? We're getting an especially great view of the Flatiron
building today because the scaffolding, which has enshrouded it for seven years, is coming down.
It's almost all the way down, and the building hasn't looked this good since it was unveiled.
All these buildings that were built at the turn of the century as offices are now at their highest
level of utility as luxury housing. People want to live in that facade. We are in Soho. We just
got out of the F train at the Broadway Lafayette stop. This is one of the fashionable areas to come
shopping now. We all know that about Soho, but what Soho was was a community of about 400 cast iron
manufacturing buildings. The story about this kind of architecture is it was invented along with other
sort of industrial revolution era manufacturing techniques in order to create inexpensive
prefab buildings. It really, in a way, changed working conditions. Even though nobody much
cared about working conditions in 1857, manufacturing used to be in dingy candle-lit
oil lamp rooms and suddenly became sun-flooded and quite pleasant by comparison. The windows
becoming huge is because the cast iron was much lighter than masonry and the windows could be
bigger. When this area was totally abandoned in the dark years of New York, all these buildings
were deserted and they were sort of squatted in by artists because they were incredibly cheap and
they were incredibly full of natural light. It was illegal to live in them because they were
zoned as manufacturing buildings, but the area also had no trash removal. If you stuck around,
you'd find yourself in the most desirable neighborhood in Manhattan, but that's the story
of many of the things we're looking at today. We just got off the York Street station of the
F train and we're in DUMBO. DUMBO, so called, because it's an acronym for Down Under Manhattan
Bridge Overpass. The Manhattan Bridge is behind me, so as you can see from the popularity of the
view behind me, this has become one of the great Instagrammable places in New York and tourists
come from all over the way. They used to stand in front of neon signs of Times Square and they
take this picture, as one or two people may be doing at this moment and as we are, of the bridge.
An interesting nerd ball historical detail about the Williamsburg and the Manhattan Bridge. They
both carried train tracks. The Manhattan Bridge had them on the outside edges and the Williamsburg
Bridge had the subway in the middle. The Manhattan Bridge experienced much more intense flexing
because engineering of these bridges and the weight loads of trains and stuff was still very
experimental in those days and so that caused certain issues with this bridge when it was in
use, which have been resolved. But who are you going to hear that from? Nobody? Oh, is it nobody? Me!
My favorite view is looking up under that bridge at the guts of the engineering of this incredible
piece of infrastructure. But what's under the arch? Our friend from earlier in the day, the Empire
State Building. We've taken the F train from uptown, from midtown, and now we've ended up
at the party, Coney Island. At the turn of the century, this was the largest concentration of
amusement parks in the world ever built and there were three clustered together. Dreamland, Luna Park
and the Steeplechase. You got to remember that what we're looking at is the birthplace of the
American amusement park. This is a very American idea and a Luna Park or a boardwalk like this
has become something in our consciousness that represents the American idea of a summer good
time. It was born here and this is still going. It's incredible how people fall in love with it
in every era and maybe you will too if you come here. Take the F train. Find out.
