Flatiron District Private Walking Tour: The Rise of 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 min)

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 min)

Discover the story behind the second-oldest monument in New York City and its often-overlooked significance.(5 min)

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 min)

Hear the powerful story of NYPD officer Moira Smith, a true hero of September 11th, and reflect at this moving tribute.(5 min)

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 min)

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 min)

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 min)

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 min)

Step inside the world of high justice and learn what really goes on behind the doors of this historic judicial building.(5 min)

Gaze up at America’s largest exterior clock and hear how the Great Depression altered the course of this once-grand skyscraper.(5 min)

Wrap up your journey with a look back at the luxurious Fifth Avenue Hotel and the origins of Madison Square Park.(10 min)

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 min)