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

22 Reviews 5.00 out of 5 stars Based on 22 reviews collected by Cool New York City and TripAdvisor |
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from $59 per person

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The Grand Hotel (1868)
Explore the Ruins of a Forgotten City in the Middle of Manhattan Walking Tour Image 2
The Albermerle, Hoffman House, and the Worth monument
The Wilbraham (1891), bachelor flats
A brownstone relic of a former suburban neighborhood on Fifth Avenue

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On average, this is booked 14 (0) days in advance.
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Overview

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'.

What's Included

  • Professional guide
  • Gratuities
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Meeting Location

Meeting point

5th Avenue
New York, NY 10010, USA

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Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

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What To Expect

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.
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15 minutes • Admission Ticket Free

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.
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10 minutes • Admission Ticket Free

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.
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10 minutes • Admission Ticket Free

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.
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15 minutes • Admission Ticket Free

Theodore Roosevelt Birthplace National Historic Site (Pass By)

We see how the former President's life fits in with the history
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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.
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10 minutes • Admission Ticket Free

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.
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15 minutes • Admission Ticket Free

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.
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5 minutes • Admission Ticket Free

Hotel Wolcott

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.
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10 minutes • Admission Ticket Free

Empire State Building (Pass By)

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.
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Fifth Avenue (Pass By)

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.
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230 FIFTH ROOFTOP BAR NYC (Pass By)

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

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness

Frequently Asked Questions

(7)

Q: What is the cancellation policy for the Explore the Ruins of a Forgotten City in the Middle of Manhattan Walking Tour?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (EDT).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

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Activity code: C-44899P1

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Reviews

5.00
22 reviews

Average 5.00 out of 5 stars based on 22 traveler reviews collected by Cool New York City and partner sites such as Cool Destinations and TripAdvisor

5 stars
22
4 stars
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Frequently Asked Questions (7)

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

The answers provided below were previously given in response to questions from Cool New York City customers.

Filter by:

Q: What is the cancellation policy for the Explore the Ruins of a Forgotten City in the Middle of Manhattan Walking Tour?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (EDT).
  • This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Professional guide.
The following is NOT included:
  • Gratuities.
Apr 2025
Q: What is the weather cancellation policy?
A:

This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Apr 2025
Q: What is the minimum age for this tour?
A:

The minimum age to participate is 12. This tour requires at least one adult to accompany children..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Explore the Ruins of a Forgotten City in the Middle of Manhattan Walking Tour is as follows:

  • Service animals allowed
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Explore the Ruins of a Forgotten City in the Middle of Manhattan Walking Tour will be included in your confirmation email from Cool New York City. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024

What's Included

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

  • Professional guide
  • Gratuities

Additional Info

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness

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American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

Lowest Price Guarantee

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

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  • If you find a lower retail or prepaid rate for the same tour, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Cool New York City and 48 hours before your trip starts, we will refund the difference.
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  • Cool New York City reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
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Cancellation Policy

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

Free cancellation
100% refund
No refund

You can cancel up to 24 hours in advance of the tour for a full refund.

  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (EDT).
  • This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
  • This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

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American Museum of Natural History Admission Ticket

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American Museum of Natural History Admission Ticket

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