Explore the Ruins of a Forgotten City in the Middle of Manhattan
Overview
Available languages
Mobile ticket
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'.
Additional Info
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.
What‘s Included
Professional guide
Gratuities
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.
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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Reviews
32 reviews
Total reviews and rating from Viator & Tripadvisor
Fabulous Tour!
Frank T,
Oct 23, 2025
- Review from Viator
5.00Fabulous tour! We covered so much history, and Robert was a fount of detailed knowledge about every aspect - events, people, architecture, geography and more! We liked this tour so much, we are sure to take another, weather and schedules permitting. Robert is the best!
A professional tour for locals and visitors!
Kyle M,
Sep 22, 2025
- Review from Viator
5.00Our guide, Rob, was a wealth of knowledge. A true professional who could have filled a weekslong tour with his appreciation and understanding of nearly every facet of NYC's history. Highly recommend this tour for locals and visitors alike.
Highly recommend, fascinating, it will change the way you see New York
Compass36178085091,
Aug 31, 2025
- Review from Tripadvisor
5.00The tour guide was excellent. We learned so much about the history and architecture of New York. It was interesting and fun. our guide brought it all to life while providing context and amusing anecdotes. I highly recommend
Excellent tour with local historian
kathleenfV7083IS,
Aug 30, 2025
- Review from Tripadvisor
5.00Rob is an excellent tour guide! We took his Gilded Age tour today. He is knowledgeable and thoughtfully answered our questions throughout the 3 hours we were together. He was very intune with our surroundings, blending us in with the ebb and flow of pedestrian traffic. He drew on his experience living in and observing the history of the city and combined it with thorough research into the development and changes of New York City through the c. 1840s-1900s. He shared a lot of salient photos, drawings, maps, and even directory listing to showcase the businesses and homes. We would recommend his tours!!
Great information you never knew about this part of the city!
Mary D,
Aug 27, 2025
- Review from Viator
5.00I've traveled to Manhattan and taken many tours, but truly appreciated the information and research behind it as I learned about a different city hiding in plain sight!
Nomad history
bettylinkress,
Jul 4, 2025
- Review from Tripadvisor
5.00The tour was fantastic! We learned so much about the history of NYC. Our guide Robert was very informed and so good at what he does. We highly recommend this tour.
The best tour for history and architecture heads!
askzy,
Jun 1, 2025
- Review from Tripadvisor
5.00We walked around mid town and got a very intense lesson on the history of New York City, how it relocated and moved uptown over time and left behind these gorgeous architectural gems along the way - and also tore down and rebuilt much of itself.
Great tour, so informative!
stephaniemV6746MZ,
May 19, 2025
- Review from Tripadvisor
5.00So informative! This tour was so much better than I expected it to be. Our guide had so much knowledge about the city and was very friendly and kind.
Watch Rob peel back the layers ot time in this (surprisingly) fascinating tour
kathrynrI6002VN,
May 4, 2025
- Review from Tripadvisor
5.00This tour was absolutely fascinating. Through Rob's eyes ( and historic maps and photos), you could imagine how the wealthy around 5th Ave and 20th street lived and shopped and worked and played. He set all this in the historical context of a developing city, moving northwards. Many of the historic buildings are mixed in amongst newer ones or used now for something else. You will never look at that area of the city the same way again. Very enriching.
Informative and comprehensive historical walking tour!
Tobin D,
Mar 2, 2025
- Review from Viator
5.00Fascinating history of the city was shared as we walked throughout the area around the Flatiron Building. Great photos that depicted the evolution of the neighborhood provided additional perspective. Highly recommend.
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