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

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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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