New York Flatiron District Historical Walking Tour

Discover the rich history of NYC’s Flatiron District on this top-rated, two-hour walking tour led by a licensed local guide. Visit historic sites, including the Flatiron Building, original Madison Square Garden, MetLife Tower, and locations tied to the Gilded Age, 9/11, 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. Operated by a top-rated small business, it’s a fun way to explore the city and support community-based tourism.
Guests can add on the hotel pick-up experience ($59) and Italian Marketplace experience ($19), which includes a visit to a world-renowned market offering handmade pasta, fresh cannolis, and unforgettable pizza. Food and drinks not included.

Meeting Point

Madison Square Park

11 Madison Ave, New York, NY 10010, USA

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.

What's included:

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

Not included:

• Italian Marketplace (If Option Selected)
• Hotel Pick Up & Photo Album & Additional Tour Stops (If Option Selected)

What to expect:

Duration: between 2 hours and 4 hours

Flatiron Building

175 5th Ave, New York City, 10010-7703, New York

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.

10 minutes • Admission Ticket Included

Madison Square Park

11 Madison Ave, and Madison and Fifth Avenues, New York City, 10010-3602, New York

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.

5 minutes • Admission Ticket Included

William Jenkins Worth Monument

Broadway and 24th Street, New York City, 10010, New York

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

5 minutes • Admission Ticket Included

Madison Square Park

11 Madison Ave, and Madison and Fifth Avenues, New York City, 10010-3602, New York

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.

10 minutes • Admission Ticket Included

Madison Square Park

11 Madison Ave, and Madison and Fifth Avenues, New York City, 10010-3602, New York

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

5 minutes • Admission Ticket Included

Madison Square Park

11 Madison Ave, and Madison and Fifth Avenues, New York City, 10010-3602, New York

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.

10 minutes • Admission Ticket Included

Madison Avenue

East 57 to East 86 Streets, New York City, 10022, New York

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.

15 minutes • Admission Ticket Included

Madison Avenue

East 57 to East 86 Streets, New York City, 10022, New York

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.

5 minutes • Admission Ticket Included

Madison Avenue

East 57 to East 86 Streets, New York City, 10022, New York

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.

5 minutes • Admission Ticket Included

Madison Avenue

East 57 to East 86 Streets, New York City, 10022, New York

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

5 minutes • Admission Ticket Included

MetLife Building

200 Park Ave, , New York City, 10166-0005, New York

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

5 minutes • Admission Ticket Included

Eataly

200 5th Ave, , New York City, 10010-3302, New York

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

10 minutes • Admission Ticket Included

Madison Square Park

11 Madison Ave, and Madison and Fifth Avenues, New York City, 10010-3602, New York

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.

20 minutes • Admission Ticket Included