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

37 Reviews 5.00 out of 5 stars Based on 37 reviews collected by Cool New York City and TripAdvisor | Recommended by 100% of reviewers |
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
New York City, USA

Loading Options
Don't miss out!
On average, this is booked 14 (0) days in advance.

2 to 3 hours (approx.)
Mobile ticket
Instant confirmation
Offered in: English

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
See 1 more

Meeting Location

Meeting point

175 5th Avenue
New York, NY 10010, USA

Show on Google Maps

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

End point

This activity ends back at the meeting point.

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
Read more

Safe & secure • Easy breezy • Hassle-free

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.
Read more

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.
Read more

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.
Read more

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.
Read more

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
Read more

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.
Read more

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.
Read more

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.
Read more

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.
Read more

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.
Read more

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.
Read more

230 FIFTH ROOFTOP BAR NYC (pass by)

We ends the tour at any point in Madison Square that is convent for the guests.
Read more
Show 11 more stops

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
  • This tour/activity will have a maximum of 5 travelers

Frequently Asked Questions

(7)

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

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.

Still have questions?

We're here to help.
Activity code: C-44899P1

Traveler Photos

Reviews

5.00
37 reviews

Average 5.00 out of 5 stars based on 37 traveler reviews collected by Cool New York City and partner sites such as Cool Destinations and TripAdvisor

5 stars
37
4 stars
0
3 stars
0
2 stars
0
1 star
0

Loading Options
Don't miss out!
On average, this is booked 14 (0) days in advance.

Similar Tours & Activities

New York Private Food Tour with 6+ Tastings in Greenwich Village

Join our Secret Food Tour: New York – Greenwich Village and eat your way through one of the city’s most iconic and charming neighborhoods. Guided...

3 hours 30 minutesFree Cancellation
3 hours 30 minutesFree Cancellation
3 hours 30 minutes • Free Cancellation
5.0 (123)
from
$130
New York City Live Music Sightseeing Serenade Cruise
Likely to Sell Out
Likely to Sell Out

Looking for a fun NYC date night experience? Our NYC Serenade Cruise with a host and live Jazz band aboard our 1920s style yacht is...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$134.03
Wall Street Adventure (Walking) Financial Heart of the World.

Tour and discover the secrets of Lower Manhattan where you will learn about its history, emblematic places, movie settings, series and documentaries. Delve into the...

2 hours 25 minutesFree Cancellation
2 hours 25 minutesFree Cancellation
2 hours 25 minutes • Free Cancellation
5.0 (4)
from
$35
Greenwich Village Literary Pub Crawl

A fascinating tour of the historic pubs and haunts of the the greatest literary minds of the United States, in one of the most influential...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (50)
from
$49

Travelers Who Bought This Tour Also Bought

New York Catacombs by Candlelight

Enjoy this fascinating 90 minute group tour that introduces you to all of the secrets of the Basilica of St. Patrick's Old Cathedral. Enter off...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.7 (2,864)
from
$38
New York in One Day Guided Sightseeing Tour (includes bus, walking tour and ferry ride!)
Likely to Sell Out
Likely to Sell Out

Experience the best of New York City with a knowledgeable, licensed tour guide by your side. Our guides will make your journey unforgettable as they...

6 hoursFree Cancellation
6 hoursFree Cancellation
6 hours • Free Cancellation
4.8 (13,150)
from
$99
American Dream DreamWorks Indoor Water Park Ticket

DreamWorks Water Park is North America's largest indoor water park with more than 40 rides and record-breaking slides, including the world’s tallest indoor drop slide...

1 dayFree Cancellation
1 dayFree Cancellation
1 day • Free Cancellation
4.1 (123)
from
$79.99
NYC Bus Tour of Brooklyn, Bronx, Queens: Art, Food & Sports

This bus tour spans four of New York City’s boroughs, covering everything you need to see in one day with convenient and comfortable transportation. With...

6 hoursFree Cancellation
6 hoursFree Cancellation
6 hours • Free Cancellation
4.9 (3,599)
from
$49

What's Included

Activity name

  • Professional guide
  • Gratuities

Additional Info

Activity name

  • 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
  • This tour/activity will have a maximum of 5 travelers

Report Product Issue

Activity name

Language
Currency

Site Settings

Activity name

Currency

Activity name

Activity name

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.

Sorting, ranking, and search results

Activity name

Cool New York City wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool New York City over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.