What You Will Do
This 2-3 hour guided walking tour around Madison Square Park seeks out what's left to be found of the Gilded Age city. On this tour we read the architecture and decode the street walls in a neighborhood that was once the New York's city center at the height of the Gilded Age. Where the city came from (Soho), and where it moved to (Times Square, Museum Mile, and the shops of Fifth Avenue) is integral to understanding how New York, and Madison Square, developed. You’ll learn answers to questions you didn’t know you had about New York City, and leave with the deeply satisfying sense of understanding a city that author James Baldwin called 'spitefully incoherent'.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Itinerary
Meeting Point
Meet on the Broadway-side of the triangle-shaped building
1
Flatiron Building
15 minutes
This walking tour looks at the Gilded Age that flourished in this neighborhood as a fashionable world class city center between the 1860s to the 1920s. We spend a few minutes giving context to the greater history of the city, and the role Madison Square played in its development.
2
Madison Square Park
10 minutes
Where Fifth Avenue, Broadway and 23rd Street all meet was the center of the Gilded Age. It was just becoming the new social, political, and cultural hub when the economy leapt forward in the Industrial Age (and wealth). The former patriarchy and landed elite like the Astors were out-spent by the new Industrial wealth like the Vanderbilts by a long-shot; Madison Square center stage for that social overthrow.
In addition to the social-cultural history that shone during the Gilded Age, the era and buildings that replaced it are also worth exploring, and we'll find they, too have a fascinating history and commercial business buildings that overran everything in their path. There is a logic to the history that makes the buildings of New York make sense.
3
Fifth Avenue
10 minutes
We walk the blocks of Fifth Avenue between 23rd and 18th Streets, decoding the buildings as we go, understanding the order of development. What buildings were built when, for who, and how did they changed?
Here, New York's "signature" building-type that can be found almost anywhere: the late 19th-century "state-of-the-art" steel-frame, manufacturing loft building, often in the "elongated" Beaux Arts style are examined in detail.
Later known as Paternaster Row for the home mission office buildings and their publishing operations, it was a street of class and wealth converted to office buildings that included publishers, architects, textile manufacturers, and piano salerooms. A long forgotten business district in an even longer forgotten upper class neighborhood.
4
ABC Carpet & Home
15 minutes
Broadway between Madison and Union Square only runs for six blocks, and it is the quiet heart, cocooned blind spot, in New York City today. No streetwall is more rich in fragmented French Second Empire, Beaux Arts, Neo-Classical relics. These were the elite, so-called "carriage trade" blocks of high-end shopping during the Gilded Age. This part of the Ladies' Mile Historic Shopping District did not have an elevated train, it didn't even have the grade-level horse car rails; women stepped from carriages to shop along this unusually narrow and quiet stretch of Broadway. It remains a gem locale in the city today.
5
Theodore Roosevelt Birthplace National Historic Site
We see how the former President's life fits in with the history
6
Sixth Avenue (Avenue of the Americas)
10 minutes
The blocks of Sixth Avenue from 18th to 23rd Streets are an incredibly well preserved set of old beautiful department stores and shopping emporia. This was the middle class part of town for shopping, but even some of these incredible buildings housed establishments were worthy of the carriage trade.
We learn a little about the department stores that once brought a long-lost energy to these blocks, never forgetting the architectural relics and ruins all around that tell the history of earlier times and previous occupants.
7
Sixth Avenue (Avenue of the Americas)
15 minutes
We cross 23rd street going north and enter the old "Tenderloin", the adult entertainment blocks in an era before radio and television. It is surprising to our sensibilities today that a district of saloons, brothels and gambling halls was so close to venues for the most respectable activities that attracted the most respectable citizens.
It's not surprising that fewer buildings survive on this side of 23rd Street, redlight districts are not often preserved. What structures are left standing, besides venues and houses of ill-repute, housed middle and lower-middle class neighborhoods, and large African American and Jewish communities. These blocks attach to some of the city's most salacious, deviant and scandalous stories.
that thrived for about 30 years on this side of Broadway.
8
Tin Pan Alley
5 minutes
Tin Pan Alley is one of New York's latest historic districts. For a brief period of time the heart of the American music industry was condensed into a few buildings along 28th Street between Fifth Avenue and Sixth Avenue.
Here sheet music proliferated and popular music ensued. The early marketing methods of music promoters--the many manifestations of plugging--began here.
9
10 minutes
We cross Broadway and immediately sense the historical shift in the streetwall as we walk just a few feet to Fifth Avenue, and the upper class part of town.
The Wolcott Hotel was one of over a dozen fine, Gilded Age hotels in the immediate vicinity, many now converted to SROs and city housing.
10
Empire State Building
The site of the original Waldorf-Astoria, and before that, residences of Astor brothers, the Empire State Building was the tallest building in the world for 40 years.
11
Fifth Avenue
The final leg of the tour are the blocks between the Empire State Building and the Flatiron Building. These blocks are the Rosetta Stone of New York history, containing buildings from every era passing through in the city's move uptown.
12
230 FIFTH ROOFTOP BAR NYC
We ends the tour at any point in Madison Square that is convent for the guests.
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