Textures of Two Neighborhoods: Tour of Gramercy and Flatiron Districts

The Flatiron District, located in the shadow of its glorious namesake, the Flatiron Building, is next to the enchanting Gramercy, a neighborhood that many tourists don’t get to see. On this walking tour, you’ll discover the Flatiron District's breathtaking landmarks and experience the 19th-century charm of Gramercy.

The tour starts in front of the Flatiron Building with a view of the area‘s magnificent skyline, from where you‘ll amble around Madison Square Park. As you walk, I‘ll show you a few of the district‘s secret places, including Worth Monument (a gravesite on Broadway), a statue that kept losing its glasses, and a truncated skyscraper that was supposed to tower over the world.

Your walk continues to Gramercy, an upscale neighborhood developed in the 1800s and is largely unchanged today. As you stroll around the perimeter of the exclusive Gramercy Park, you’ll pause in front of a few private clubs and residences to hear about the actors and politicians who lived here in the 1800s. The tour ends at Pete‘s Tavern, one of the oldest bars in the city that lived through Prohibition as a speakeasy.

Along the way, you‘ll:

• Hear the shocking tale of a prominent architect’s murder
• Find out the story of politician Samuel Tilden, who won the popular vote by 51% but lost the presidency in one of the most controversial elections in U.S. history
• Learn how to check if the mayor is home according to an old Dutch custom
• Spot colossal clocks atop the Metlife building tower that surpass Big Ben in size
• Marvel at Church Missions House, the iconic building featured in the hit Netflix series Inventing Anna
• Admire the National Arts Club, a private institution with an illustrious history and three U.S. presidents among its members
• Meet Edwin Booth, America‘s greatest Hamlet performer and the brother of President Lincoln‘s assassin
• Raise a glass to O. Henry who penned his beloved story The Gift of the Magi at Pete‘s Tavern

Join me on this fascinating hour-long walk through two historic, less-traveled New York neighborhoods with such different textures. It‘s a short walk, but take it slow and enjoy the rich interplay of history, architecture, and culture, all within a few city blocks.