• Flatiron Building - Begin the tour at one of New York City’s most iconic architectural marvels, where you’ll discover how this innovative structure became a symbol of the city.
• Madison Square Park - Delve into the life of New York’s former Governor and U.S. Secretary of State, renowned for “Seward’s Folly” and his involvement following the Lincoln assassination.
• William Jenkins Worth Monument - Uncover the history of New York City’s second-oldest monument and its often-overlooked importance.
• Madison Square Park - Enter the fascinating world of the Gilded Age with tales of scandal, America’s first supermodel, and the notorious “Murder of the Century” depicted on the Gilded Lady mural.
• Madison Square Park - Listen to the inspiring story of NYPD officer Moira Smith, a true hero of September 11th, and reflect at this poignant tribute.
• Madison Square Park - Discover how Henry Bergh established the nation’s first animal protection organization, transforming our perspective on animal welfare, as you visit a 19th-century ASPCA building.
• Madison Avenue - Investigate the rich 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 - Learn about the Jerome family and their unexpected connections to American history, including links to Winston Churchill at the site of the Jerome Mansion.
• Madison Avenue - Visit a solemn memorial inspired by the gas chambers at Auschwitz and understand why it was placed on one of NYC’s most ornate court buildings.
• Madison Avenue - Explore the realm of high justice and discover what truly happens behind the doors of this historic judicial building.
• MetLife Building - Admire America’s largest exterior clock and learn how the Great Depression changed the fate of this once-majestic skyscraper.
• Eataly - Conclude your journey with a reflection on the opulent Fifth Avenue Hotel and the beginnings of Madison Square Park.
• Madison Square Park - Participants can opt for the two-hour Historical Walking Tour ($39) or enhance their experience with the Tour + Italian Marketplace option ($19), which includes a visit to a world-famous Italian marketplace celebrated for its culinary delights—from handmade pasta and fresh cannolis to unforgettable pizza. After the tour, there will be time to explore, shop, or enjoy a delightful meal at your own pace. Please note: food and drinks are not included in the upgrade price.

• Public transportation (bus, subway, cable car, etc.)
• Photos from the Library of Congress

• Gratuities
• Meals

Explore the fascinating history of New York City’s Flatiron District on this highly-rated, two-hour walking tour, guided by a licensed local expert. Discover historic landmarks such as the Flatiron Building, the original Madison Square Garden, MetLife Tower, and sites associated with the Gilded Age, 9/11, Nikola Tesla, and Lincoln’s assassination. Listen to captivating stories about notable figures like Cornelius Vanderbilt, P.T. Barnum, and Edith Wharton, enhanced with archival photographs. The tour is short and comfortable, with opportunities to sit and relax. Perfect for history enthusiasts and architecture fans, this engaging experience combines storytelling, rare visuals, and iconic sites. Run by a top-rated small business, it offers a delightful way to explore the city while supporting local tourism.

Check out our options and find the perfect fit for you!

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