Scavenger Hunts in the Flatiron District | NYC

Scavenger Hunts in The Flatiron District

  • private
  • adults
  • kids
  • outdoor

The Flatiron District Dash Scavenger Hunt

Secrets to seek, from Union Square to Madison Square Park

In this unusual game, you and your team will take on a series of fun and funny team-building challenges in and around Madison Square Park, Gramercy Park, Union Square, and Broadway that highlight the neighborhood’s hidden history and most surprising sights.

Strategy is crucial: which mix of the three kinds of challenges and what route will combine to produce victory? First and foremost, you’ll follow clues to track down fascinating places and find answers to tricky questions about them. You might find points among the carnival of gourmet food shops that is Eataly, or discover movie locations from such movies as Spider-Man, or dig into history outside Theodore Roosevelt’s childhood home  and grand buildings that once made up “the Ladies’ Mile.”

You might tackle such questions as…

  • Find a store that sounds like it sells shards from a Hollywood studio. Nearby, what year did some pirates from Penzance arise here? Answer: A sign next to Rosen Paramount Glass reads, “On this site Sir Gilbert Sullivan composed ‘The Pirates of Penzance’ in 1879.” 
  • One building facing Madison Square Park suffers from stunted growth. It was supposed to climb 100 stories to become the tallest in the world—but money ran out after the 1929 market crash. The semi-tower’s predecessor across the street was the tallest in the world (1909–13). It too has played a role in movies, including After Hours. After hours, whose chorus chimes? Answer: A chorus from Handel chimes, as noted on a Met Life Building plaque.

You’ll also search for opportunities to tackle Team Photo Challenges, requiring sharp eyes and creative minds. And along the way don’t forget to find the objects you must collect or create. Rounding out the game, you’ll meet up with our Hunt Host for a surprise bonus challenge.

Even if you don’t win (but of course you will, right?), you’ll be surprised at all the cool places you visit and the fun you have with your teammates.


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  • private
  • adults
  • outdoor

Union Square to Madison Square: Roosevelt’s Rambles Scavenger Hunt

Hunt where presidents roamed and artists ambled

Teddy Roosevelt grew up on 20th Street near Broadway, back when the stretch between Union Square and Madison Square Park was New York City’s epicenter of power, fame, and talent. On this team-building scavenger hunt, you’ll travel back in time to the Gilded Era and see this area the way Roosevelt saw it.

Highlights include presidential sites linked to Washington, Lincoln, Kennedy, and Cleveland, as well as two men who lost the presidency (Horace “Go west, young man” Greeley and Samuel Tilden, who won the popular vote but lost the election).

But there’s more than just the past to track down on this varied hunt. You’ll also search for Andy Warhol’s famed Factory, James Cagney’s Gramercy Park home, Humphrey Bogart’s wedding place, movie locations used by Martin Scorsese and Woody Allen, and a bar where O. Henry wrote. Plus, you’ll see where the Sex and the City gals sipped cocktails, Shaft took on a murder case, Spider-Man reported to work, Godzilla rampaged, and meteorites announced Armageddon.

You might tackle such questions as…

  • The namesake for Irving Place and the nearby high school supposedly lived in a house at Irving and 17th Street—but there’s no actual proof of that. Who’s always chased by Jack? Answer: A plaque honoring Washington Irving includes Ichabod Crane, chased by the Headless Horseman, who brandishes a jack-o’-lantern.
  • The National Arts Club occupies the former mansion of Samuel J. Tilden, who in 1876 became the first presidential candidate to win the popular vote but lose the election—in his case, to Rutherford B. Hayes. In more recent years, the house appeared in the movies The Age of Innocence and Manhattan Murder Mystery. The man who founded the Players Club next door, actor Edwin Booth (that’s him as Hamlet in the middle of Gramercy Park), was the brother of Lincoln assassin John Wilkes Booth. But what writer gets top billing outside the National Arts Club? Answer: Shakespeare appears at the top left of a relief with the heads of famous writers on the facade of the club.

No prior knowledge is necessary—just sharp eyes, comfy shoes, and a love of adventure.


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