A Tale of Three NYC Squares: Union Square, Gramercy Park, & Madison Square

Nestled among Midtown Manhattan’s busy streets are three squares with stories as captivating as the city itself. How did each come to exist and develop into either exclusive residential areas, commercial enterprises, home to artists, or sites for public demonstrations? Get ready to hit the streets and uncover the layers of history and culture that make each square a true New York treasure.

Join New York Adventure Club as we journey through three celebrated squares in Manhattan — Union Square, Gramercy Park, and Madison Square — to explore how their fascinating past, unique architecture, and cultural influence shaped New York.

Led by licensed tour guide and native New Yorker Richard Soden, this specially curated walking tour featuring serene parks to bustling plazas will include:

• A visit to Union Square's notable statues including Washington, Lincoln, Gandhi, and Marquis de Lafayette
• A discussion on Tammany Hall and a glimpse at its former headquarters
• A stop by Pete’s Tavern, the historic pub where O. Henry is believed to have written The Gift of the Magi
• A peek at Gramercy Park through the gates, Manhattan’s only private and gated garden
• A walk past Theodore Roosevelt's former home
• A stroll down "The Historic Ladies’ Mile," once home to Manhattan’s trendsetting stores
• A look at iconic sites in and around Madison Square, including the Flatiron Building, Worth Monument, and original sites of the first two Madison Square Garden buildings

See you there!

*Please bring a water bottle and comfortable pair of shoes as we’ll be doing a lot of walking!

**This experience ends at Madison Square Park

About Richard

"I am a native New Yorker who was born and have lived on the lower east side all my life. I love this city and all its beauty and peculiarities, and I love sharing it with native New Yorkers, newcomers, and returning visitors. I enjoy telling stories which I'll share with you. You’ll learn the many secrets about the city I call 'home.'"

Disclaimer

Event takes place rain or shine.

By attending a New York Adventure Club experience, you accept our terms of service.

Categories: In-Person, Neighborhood Tours

Event Venue & Nearby Stays

Torch & Crown Brewing Union Square (Outside Restaurant), 20 Union Square West, New York, United States