Flatiron District Private Walking Tour: The Rise of New York

2 hours Free cancellation Private tour

The Gilded Lady — Photos: the activity supplier, via Viator

About this activity

Discover the rich history of NYC’s Flatiron District on this top-rated, two-hour walking tour led by a licensed local guide and college history professor with a doctorate in Education.

Visit historic sites, including the Flatiron Building, original Madison Square Garden, MetLife Tower, and locations tied to the Gilded Age, Nikola Tesla, and Lincoln’s assassination. Hear stories about figures like Cornelius Vanderbilt, P.T. Barnum, and Edith Wharton, brought to life with archival photos.

The route is short and comfortable, with spots to sit and relax. Ideal for history lovers and architecture buffs, this immersive experience blends engaging storytelling, rare visuals, and iconic landmarks.

This is a private tour tailored to your interests. Your reservation will serve a placeholder. After you book, I will contact you to arrange a date and time convenient to you.

Private and Luxury Private Sightseeing Tours Historical Tours Walking Tours Nature Walks New Product Short term availability Weather Dependent - Moderate

At a glance

Duration: 2 hours
Confirmation: Instant confirmation
Ticket: Mobile or paper ticket accepted
Group: Your group only
People per booking: 1–12
Guide: English
Operated by: Epic Walking Tours

Ages: Adults (10–99 years)

What is included

Included

Included: This walking tour includes visits to historic locations in the Flatiron District.
Included: This tour is private and customized to your interests.

Not included

Not included: Gratuities

Itinerary

Flatiron Building

10 min Admission included

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.
Madison Square Park

5 min Admission included

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.
William Jenkins Worth Monument

5 min Admission included

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

10 min Admission included

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.
Madison Square Park

5 min Admission included

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

10 min Admission included

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.
Madison Avenue

15 min Admission included

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.
Madison Avenue

5 min Admission included

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.
Madison Avenue

5 min Admission included

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.
Madison Avenue

5 min Admission included

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

5 min Admission included

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

10 min Admission included

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

20 min Admission included

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.

Meeting point and pickup

Everyone meets at the meeting point.

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.

End point

The tour concludes at the iconic Flatiron Building.

Cancellation

Free cancellation

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

If you cancel	You get back
At least one day before	100%
Less than a day before	0%

The operator may cancel if the weather does not allow it; you then get another date or your money back.
The operator may cancel if too few people book; you then get another date or your money back.