The Squares That Shaped Manhattan: Gramercy, Madison & Union

New To The Site! New York City, USA

Loading Options

2 hours (approx.)
Mobile ticket
Instant confirmation

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
See 1 more

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

Union Square

Tour Union Square and learn its history, explore the surrounding buildings, and learn about the famous monuments in Union Square
Read more

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
Read more

10 minutes • Admission Ticket Free

Gramercy Park

Tour Gramercy Park and learn its history.
Read more

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
Read more

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
Read more

35 minutes • Admission Ticket Free

Show 3 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

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 (EST). 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-327869P9


Loading Options

Similar Tours & Activities

Contrasts VIP Private (We visited Harlem, Bronx, Queens, Brooklyn and Manhattan)

Contrasts VIP Private (We visited Harlem, Bronx, Queens, Brooklyn and Manhattan)

1
 6 hours  Hotel pickup offered  Free Cancellation  Instant Confirmation
from
$165

NYC Central Park Horse and Carriage Ride: Long Ride 45 min
Likely to Sell Out

NYC Central Park Horse and Carriage Ride: Long Ride 45 min

5
 45 minutes  Free Cancellation  Instant Confirmation
from
$190

Guided Bike Tour Of Central Park

Guided Bike Tour Of Central Park

 2 hours  Free Cancellation  Instant Confirmation
from
$49

Luxury Private Tour in New York City by Vehicle with Tour Guide

Luxury Private Tour in New York City by Vehicle with Tour Guide

1
 4 hours  Hotel pickup offered  Free Cancellation  Instant Confirmation
from
$2,300

Travelers Who Bought This Tour Also Bought

American Dream DreamWorks Indoor Water Park Ticket
Likely to Sell Out

American Dream DreamWorks Indoor Water Park Ticket

 1 day  Free Cancellation  Instant Confirmation
from
$69

American Dream Nickelodeon Universe Indoor Theme Park Ticket
Likely to Sell Out

American Dream Nickelodeon Universe Indoor Theme Park Ticket

 1 day  Free Cancellation  Instant Confirmation
from
$62.91

Circle Line: 2.5hr - Complete Manhattan Island Cruise

Circle Line: 2.5hr - Complete Manhattan Island Cruise

 2 hours 30 minutes  Free Cancellation
from
$37.20

What's Included

Activity name

  • Guided Walking Tour
  • 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

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 (EST).

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.