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

This 2-hour guided walking tour around Madison Square Park seeks out what's left to be found of the Gilded Age city, reading the architecture and decoding the street walls in a neighborhood that was once the city center.  Where the city came from (Soho), and where it moved to (Times Square, Museum Mile, and the shops of Fifth Avenue), is explained in short order. 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'.


90 to 120 minutes


Mobile ticket

  • What's included :
    • Professional guide
    What's excluded :
    • Gratuities
  • This is a typical itinerary for this product

    Stop At: Flatiron Building, 175 5th Ave At 23rd St., New York City, NY 10010-7703

    This walking tour looks at the Gilded Age that flourished in this neighborhood as a fashionable world class city center from the 1870s to the 1910s. We spend a few minutes at the start of the tour giving it a context within the greater history.

    Duration: 20 minutes

    Stop At: Madison Square Park, Between 23rd and 26 streets and Madison and Fifth Avenues, New York City, NY 10010

    We look and learn at how history evolved to create the city streetscapes around the park today.

    Duration: 5 minutes

    Stop At: Fifth Avenue, 5th Ave, New York City, NY 10118-4810

    We walk the blocks of Fifth Avenue between 23rd and 18th Streets, decoding the buildings as we go. What they were built for, how they have changed. This went from an upper class residential history to an upper class carriage trade/manufactoring center. A beautiful array of Beaux Arts, earlier era, business district buildings.

    Duration: 10 minutes

    Stop At: 599 Broadway, New York City, NY 10012-3235

    Broadways fascinating "mixed use" history along the few blocks between Madison Square and Union Square, where old modest homes and mansions mixed incredible French Second Empire style and Beaux Arts buildings from an earlier era.

    Duration: 10 minutes

    Pass By: Theodore Roosevelt Birthplace National Historic Site, 28 E 20th St between Broadway and Park Avenue South, New York City, NY 10003-1311

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

    Stop At: Sixth Avenue (Avenue of the Americas), New York City, NY

    The blocks of Sixth Avenue from 18th to 23rd Streets are an incredibly well preserved set of old beautiful department stores and shopping emporia.

    Duration: 10 minutes

    Stop At: Sixth Avenue (Avenue of the Americas), New York City, NY

    We then cross 23rd street going north and enter into the old Tenderloin, the adult entertainment part of town in an era before television, radio, and even telephones, that thrived for about 30 years on this side of Broadway.

    Duration: 15 minutes

    Stop At: Hotel Wolcott, 4 W 31st St, New York, NY 10001, USA

    A jewel of the Gilded Age is the lobby and restaurant/ballroom of the Hotel Wolcott. The over-the-top, incredible interiors are representative of a number of such relics in the area.

    Duration: 20 minutes

    Pass By: 230 FIFTH ROOFTOP BAR NYC, 230 5th Ave Corner 27th street on 5th ave, New York City, NY 10001-7704

    Simply pass by

    Pass By: 599 Broadway, New York City, NY 10012-3235

    We then cross over Broadway, back to the (historically) more respectable part of town.

    Pass By: Fifth Avenue, 5th Ave, New York City, NY 10118-4810

    The final leg of the tour are the 10 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: Manhattan Unlocked Historical and Architectural Walking Tours, Times square New York, New York, New York City, NY 10036

    Manhattan Unlocked Tours lets the built environment, that is, the architectural makeup of the streetscapes, tell the history of New York City.

    Pass By: Empire State Building, 20 West 34th Street, New York City, NY 10001

    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.

  • Departure Point :
    175 5th Ave, New York, NY 10010, USA
    Return Detail :
    Returns to original departure point
    Hotel Pickup :
    • Confirmation will be received at time of booking
    • Wheelchair accessible
    • Stroller accessible
    • Service animals allowed
    • Near public transportation
    • Infants must sit on laps
    • Travelers should have a moderate physical fitness level
    • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
    • This experience 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
    • This tour/activity will have a maximum of 15 travelers
  • You can present either a paper or an electronic voucher for this activity.
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.



Age Req.


Fitness Req.


Group Size


Organised by Manhattan Unlocked Historical and Architectural Walking Tours

Activity ID: V-44899P1

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