Adventure Collective
Historic Landmarks & Urban Walks with Eyes on Manhattan - New York City

Historic Landmarks & Urban Walks with Eyes on Manhattan

New Yorkeasy

Difficulty

easy

Duration

2 hours

Fitness Level

All fitness levels; comfortable walking needed

Overview

Discover the stories behind NYC’s most famous squares—Gramercy Park, Union Square, and Madison Square Park—on this immersive guided walk led by expert Richard Soden. Dive into history, architecture, and the city’s ever-changing landscape.

New York, New York

A Tale of Three New York City Squares: Gramercy Park, Madison Square & Union Square

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About This Adventure

Embark on a captivating walking tour through Manhattan's iconic squares—Gramercy Park, Union Square, and Madison Square Park. Led by expert Richard Soden, discover the rich history, famous monuments, and vibrant transformations of these areas. Experience the charm of historic buildings and learn about their impact on New York City’s culture.

New York City has many unique squares each with its own unique history and culture. We’ll explore peaceful Gramercy Park and its surrounding historic buildings, the busy and crowded Union Square, and the numerous monuments and buildings surrounding Madison Square Park. This walk traces how each of these squares came to exist and developed into either exclusive residential areas, commercial enterprises, home to artists, and sites for public demonstrations. Along the walk, we will stop many historic buildings that helped shape New York City.

Journey through three unique squares in Manhattan and visit some of the neighborhood’s famous sites and attractions. You’ll learn about the transformation that has occurred in each square over the past several generations.

Led by prominent neighborhood expert, Richard Soden, a custom-made walking tour will include:

  1. Pass by famous statues in Union Square including Washington, Lincoln, Gandhi, and Marquis de Lafayette
  2. Learn about “Tammany Hall” and see where its headquarters were
  3. Visit the outside of the historic Pete’s Tavern where O’Henry may have written the “Gift of the Magi”
  4. See the only private and locked garden in Manhattan (Gramercy Park)
  5. Pass by the home of Theodore Roosevelt
  6. Walk along the “The Historic Ladies Mile” where fashionable stores once stood
  7. See the famous Flatiron Building
  8. Learn who’s buried in the Worth Monument
  9. Pass by the original locations of Madison Square Gardens
  10. Stroll through Madison Square Park and see the many statues

Adventure Tips

Wear comfortable walking shoes

The tour covers multiple blocks, so sturdy shoes are recommended for comfort.

Bring a camera or smartphone

Capture the stunning architecture and lively street scenes.

Check the weather forecast ahead of time

Be prepared for outdoor walking in various weather conditions.

Arrive early to secure a good spot

Join promptly to fully enjoy the guided experience and mingle with other visitors.

Local Insights

Wildlife

  • Pigeons
  • Squirrels

History

The parks have played pivotal roles in New York’s social and political history, serving as gathering points for protests and celebrations.

Conservation

The parks are maintained with sustainability in mind, focusing on green space preservation and urban habitat support.

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Adventure Hotspots in New York City

Frequently Asked Questions

Recommended Gear

Comfortable walking shoes

Essential

Supports extended walking and keeps your feet comfortable.

Weather-appropriate clothing

Essential

Prepared for varying weather conditions during outdoor walking.

spring|summer|fall|winter specific

Water bottle

Essential

Stay hydrated during the tour.

Notebook or mobile device for notes/photos

Capture interesting details and memories.