Explore the Ruins of a Forgotten City in the Middle of Manhattan

Tour at a glance

Itinerary

1. 1
   Flatiron Building

   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.

   15 min Admission free
2. 2
   Madison Square Park

   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.

   10 min Admission free
3. 3
   Fifth Avenue

   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.

   10 min Admission free
4. 4
   ABC Carpet & Home

   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.

   15 min Admission free
5. 5
   Theodore Roosevelt Birthplace National Historic Site

   We see how the former President's life fits in with the history

   Pass by (no stop) Admission free
6. 6
   Sixth Avenue (Avenue of the Americas)

   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.

   10 min Admission free
7. 7
   Sixth Avenue (Avenue of the Americas)

   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.

   15 min Admission free
8. 8
   Tin Pan Alley

   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.

   5 min Admission free
9. 9

   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 min Admission free
10. 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.

    Pass by (no stop) Admission free
11. 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.

    Pass by (no stop) Admission free
12. 12
    230 FIFTH ROOFTOP BAR NYC

    We ends the tour at any point in Madison Square that is convent for the guests.

    Pass by (no stop) Admission free

Meeting & pickup

Everyone meets at the start point.

Schedule

Good to know

• Service animals allowed
• Public transportation options are available nearby
• Travelers should have at least a moderate level of physical fitness

Cancellation policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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