Flatiron Gilded Age Walking Tour: Architecture, Scandals, & Food

New York, US

Included

  • inclusion
    This walking tour includes visits to historic locations in the Flatiron District.

Excluded

  • exclusion
    Meals
  • exclusion
    Gratuities

Meeting Point

Please meet your guide in front of Jemmy's Dog Run, located on the west side inside Madison Square Park. Look for the guide with an Epic Walking Tours flag for easy identification.

Meeting point

11 Madison Ave, New York, NY 10010 , United States

End point

End Point

The tour concludes at the iconic Flatiron Building.

Meeting point

175 5th Ave, New York, NY 10010 , United States

End point

What to expect

1
Flatiron Building

Your tour begins at one of NYC’s most iconic architectural landmarks, where you’ll learn how this groundbreaking structure became a symbol of New York itself.

Duration 10 minutes
Admission Admission Included
2
Madison Square Park

Uncover the life of New York’s former Governor and U.S. Secretary of State—best known for "Seward’s Folly" and his role in the aftermath of the Lincoln assassination.

Duration 5 minutes
Admission Admission Included
3

William Jenkins Worth Monument

Discover the story behind the second-oldest monument in New York City and its often-overlooked significance.

Duration 5 minutes
Admission Admission Included
4
Madison Square Park

Step into the intrigue of the Gilded Age with stories of scandal, America’s first supermodel, and the infamous “Murder of the Century” as shown on the Gilded Lady mural.

Duration 10 minutes
Admission Admission Included
5
Madison Square Park

Hear the powerful story of NYPD officer Moira Smith, a true hero of September 11th, and reflect at this moving tribute.

Duration 5 minutes
Admission Admission Included
6
Madison Square Park

Learn how Henry Bergh founded the nation’s first animal protection organization and changed the way we view animal welfare forever as you visit a 19th century ASPCA building.

Duration 10 minutes
Admission Admission Included
7

Madison Avenue

Explore the layered history of the New York Life Insurance Building site—from the original Roman Hippodrome and P.T. Barnum’s circus to the original Madison Square Garden.

Duration 15 minutes
Admission Admission Included
8

Madison Avenue

Peek into the lives of the Jerome family and their surprising connections to American history, including ties to Winston Churchill at the site of the Jerome Mansion.

Duration 5 minutes
Admission Admission Included
9

Madison Avenue

Visit a haunting memorial modeled after the gas chambers at Auschwitz and discover why it was placed on one of NYC’s most ornate court buildings.

Duration 5 minutes
Admission Admission Included
10

Madison Avenue

Step inside the world of high justice and learn what really goes on behind the doors of this historic judicial building.

Duration 5 minutes
Admission Admission Included
11
MetLife Building

Gaze up at America’s largest exterior clock and hear how the Great Depression altered the course of this once-grand skyscraper.

Duration 5 minutes
Admission Admission Included
12

Eataly

Wrap up your journey with a look back at the luxurious Fifth Avenue Hotel and the origins of Madison Square Park.

Duration 10 minutes
Admission Admission Included
13
Madison Square Park

Guests can choose between the two-hour Historical Walking Tour ($39) or upgrade to the Tour + Italian Marketplace experience ($19), which includes a visit to a world-renowned Italian marketplace known for its culinary treasures—from handmade pasta and fresh cannolis to unforgettable pizza. After the tour, you’ll have time to explore, shop, or enjoy a delicious meal at your leisure. Please note: food and drinks are not included in the upgrade price.

Duration 20 minutes
Admission Admission Included

The experience can be subject to change due to bad weather or unforseen circumstances. We always endeavour to give you the best possible experience.

Additional Information

  • Additional information
    All areas and surfaces are wheelchair accessible
  • Additional information
    Infants and small children can ride in a pram or stroller
  • Additional information
    Public transportation options are available nearby
  • Additional information
    Service animals allowed
  • Additional information
    Suitable for all physical fitness levels
  • Additional information
    Transportation options are wheelchair accessible
  • Additional information
    Wheelchair accessible
Provided by Epic Walking Tours

What our experts say

  • icon
    Visit nearby Eataly for lunch.
  • icon
    Check out Madison Square Park's art.
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    Bring a camera for stunning views.
  • icon
    Wear comfortable shoes for walking.
  • icon
    Consider a visit to the MetLife Building.

More About this Experience

Introduction

Discover the enchanting stories and architectural wonders of New York City’s Flatiron District on this captivating two-hour walking tour. Led by a knowledgeable local guide, participants will explore over 20 iconic sites, including the stunning Flatiron Building, the historic original Madison Square Garden, and the MetLife Tower. This walking tour is not just a leisurely stroll; it’s a journey through time. With engaging storytelling and over 100 archival photos, guests will learn about pivotal moments in history connected to the Gilded Age, the tragic events of 9/11, and even the assassination of President Lincoln. The walk follows a comfortable route through the picturesque Madison Square Park, where there are numerous spots to relax and soak in the vibrant atmosphere of one of NYC's most cherished neighborhoods. Whether you're a history buff, an architecture lover, or just looking for an exciting day out, this tour promises a rich experience filled with discovery.

What to expect?

Participants can anticipate an immersive experience that combines fascinating historical narratives with the stunning architecture of the Flatiron District. Each stop on the tour reveals a different chapter of the area’s storied past, from the intriguing tales of Cornelius Vanderbilt and P.T. Barnum to the impactful legacy of NYPD officer Moira Smith during the events of September 11th. The guide will share captivating anecdotes that bring life to the historical sites, making the past feel immediate and relatable. With a focus on comfort, the route is designed for all fitness levels, ensuring that everyone can participate. Guests are invited to take a moment to sit and absorb their surroundings, making this tour not just informative but also a relaxing way to explore one of NYC's most vibrant districts. With a small group format, interactions with the guide are personal, allowing for questions and deeper conversations about the rich tapestry of history that envelops this iconic neighborhood.

Who is this for?

The Flatiron District Historic Walking Tour is perfect for a wide array of audiences. History enthusiasts will delight in the in-depth exploration of significant events and figures that shaped New York City. Architecture aficionados will appreciate the opportunity to witness the stunning designs of landmarks such as the Flatiron Building and MetLife Tower up close. Families can enjoy this tour as it caters to all ages, with stroller accessibility and a comfortable pace that ensures everyone stays engaged and entertained. Couples looking for a unique date idea will find this tour to be a charming way to spend time together while learning about the city’s rich heritage. Even solo travelers will find camaraderie among fellow adventurers, making it an inclusive experience for anyone curious about the stories behind the structures that make NYC so iconic.

Why book this?

This walking tour stands out for its unique combination of historical depth, personal storytelling, and the chance to support a local business dedicated to community-based tourism. Operated by a highly rated small business, the tour not only offers a fun and educational experience but also connects participants with the vibrant local culture. The expertise of the licensed guide transforms each landmark into a living story, rather than just a name on a map. The immersive nature of this tour allows guests to engage with the past in a way that larger, more commercial tours cannot. By choosing this experience, participants are not only enriching their understanding of NYC but are also making a conscious choice to support independent tourism, ensuring that the stories of the Flatiron District continue to be shared for generations to come.

Good to know

Before setting off on the Flatiron District Historic Walking Tour, it’s helpful to be aware of a few essential details. The meeting point is conveniently located in Madison Square Park, making it easy for participants to find their guide. The tour is fully accessible, accommodating wheelchairs and strollers, ensuring that everyone can take part in this historical journey. Each stop is thoughtfully planned to allow for moments of rest and reflection, with ample opportunities to snap photos and soak in the sights. While public transportation options are nearby, it's recommended to wear comfortable shoes as the tour involves plenty of walking. Guests are encouraged to bring along a water bottle to stay hydrated during the tour. After the tour concludes at the iconic Eataly marketplace, participants have the perfect opportunity to relax, explore, and indulge in some delightful culinary treats to round off their experience.

Reviews

Reviews for the Flatiron District Historic Walking Tour have been overwhelmingly positive, with guests praising the engaging storytelling and the depth of historical knowledge provided by the guide. Many have expressed how the combination of fascinating narratives and stunning visuals made the tour unforgettable. Participants have enjoyed the small group setting, which allowed for personal interactions and a more intimate experience. Families have highlighted the tour's accessibility and how it kept children entertained and curious about the city’s history. Overall, feedback reflects a high level of satisfaction, with many guests recommending this tour as a must-do for anyone looking to explore New York City beyond the surface. People have left the tour feeling enriched, inspired, and with a newfound appreciation for the stories and architecture that define the Flatiron District.

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