The Squares That Shaped Manhattan: Gramercy, Madison & Union

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2 hours (approximately)
Offered in: English

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

Meeting and pickup

Meeting point

Meet in front of Norstrom Rack

End point

Itinerary

Duration: 2 hours (approximately)
  • 1
    Union Square

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

    25 minutes • Admission ticket free
  • 2

    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

    10 minutes • Admission ticket free
  • 3

    Tour Gramercy Park and learn its history.

    15 minutes • Admission ticket free
  • 4
    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

    25 minutes • Admission ticket free
  • 5
    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

    35 minutes • Admission ticket free

Additional info

  • Service animals allowed
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
Supplied by Richard Soden

Tags

Historical Tours
Walking Tours
Likely to Sell Out
Small Group
New Product

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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