Broadway Top 10 CityPASS®

The Squares That Shaped Manhattan: Gramercy, Madison & Union

New To The Site! New York City, USA
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from $249 per group (up to 8)

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2 hours (approx.)
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Instant confirmation
Offered in: English

Overview

Step back in time and explore three of New York City’s most influential public spaces—Union Square, Madison Square, and Gramercy Park. Each of these iconic squares tells a story of how Manhattan transformed from a bustling 19th-century city into a modern metropolis.

Begin at Union Square, once the stage for political rallies, labor movements, and social reform, now a thriving hub of markets, art, and activism. Continue north to the refined enclave of Gramercy Park, Manhattan’s only private park, whose leafy streets and preserved architecture reflect the city’s aspiration for exclusivity, elegance, and community. Finally stroll past the "Ladies Mile" on route to Madison Square, where the elegant park was once home to the original Madison Square Garden and surrounded by Gilded Age hotels, theaters, and mansions.

Uncover stories of visionaries, politicians, artists, and everyday New Yorkers who shaped these squares into enduring landmarks of culture, history, and urban design.

What's Included

  • Guided Walking Tour
  • Gratuities
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Meeting Location

Meeting point

East 14th Street
New York, NY 10003, USA

Show on Google Maps

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

End point

Broadway
New York, NY 10010, USA

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.
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Safe & secure • Easy breezy • Hassle-free

Union Square

Tour Union Square and learn its history, explore the surrounding buildings, and learn about the famous monuments in Union Square
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25 minutes • Admission Ticket Free

Irving Plaza

Stroll down to Irving Place and see the historic sites including the presumed place where Washington Irving wrote several books, where O’Henry lived, and the historic Pete’s Tavern
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10 minutes • Admission Ticket Free

Gramercy Park

Tour Gramercy Park and learn its history.
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15 minutes • Admission Ticket Free

Flatiron Building

Stroll down a portion of the Ladies’ Mile and see former sites of Arnold Constable and Lord and Taylor and walk about the Flatiron Building
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25 minutes • Admission Ticket Free

Madison Square Park

Explore Madison Square Park and learn about its monuments See the site of the first lite Christmas Tree and learn about the “Star of Hope”, a Holocaust Memorial and the the site of the two Madison Square Gardens
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35 minutes • Admission Ticket Free

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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

(6)

Q: What is the cancellation policy for the The Squares That Shaped Manhattan: Gramercy, Madison & Union?

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). 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?

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Activity code: C-327869P9


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Frequently Asked Questions (6)

Activity name

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 The Squares That Shaped Manhattan: Gramercy, Madison & Union?
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).
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Guided Walking Tour.
The following is NOT included:
  • Gratuities.
Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure..

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 The Squares That Shaped Manhattan: Gramercy, Madison & Union 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 The Squares That Shaped Manhattan: Gramercy, Madison & Union 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

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  • Guided Walking Tour
  • Gratuities

Additional Info

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  • 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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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).

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Cool Rewards

  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
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  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
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