Landmarks
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Food
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100

This historic Montauk structure, authorized by George Washington, is the oldest of its kind in NY State

What is the Montauk Lighthouse?

100

This 1886 gift from France was assembled on what was once called Bedloe’s Island.

What is the Statue of Liberty?

100

“Piano Man” himself—born in the Bronx but raised in Hicksville.

Who is Billy Joel?

100

A weekend staple across Long Island, this breakfast item is often ordered as a "BEC".

What is a bagel?

100

This NBA team plays at Madison Square Garden and is famous for 1990s rivalries with the Bulls and Pacers.

Who are the New York Knicks?

200

You can climb 377 steps—or take an elevator—to the crown of this famous NYC landmark.

What is the Statue of Liberty?

200

This famous Colonial-era road once connected Queens to eastern Long Island and still exists today as a major thoroughfare.

What is Jericho Turnpike?

200

This comedian from Lynbrook is known for his role on SNL’s “Weekend Update” and “Staten Island Summer.”

Who is Colin Jost?

200

Often found in every Italian bakery from Queens to Montauk, these cookies are made with almond paste and layered with jam.

What are rainbow cookies?

200

This Yankees legend was the first MLB player to ever have his number retired—number 4—in 1939.

Who is Lou Gehrig?

300

You can walk above city traffic on this elevated former rail line that runs through Chelsea and the Meatpacking District.

What is the High Line?

300

In 1927, Charles Lindbergh departed for his historic transatlantic flight from this LI location, now a shopping mall.

What is Roosevelt Field?

300

This actor from Long Island became famous in the 1980s for playing a young underdog who learns karate from a wise mentor.

Who is Ralph Macchio?

300

Known across NYC delis, this sandwich features chopped beef, onions, cheese, and often mayo and ketchup, all served on a hero roll.

What is a chopped cheese?

300

Before moving to Brooklyn, this NHL team played in Long Island’s Nassau Coliseum and featured the famed “Core of Four.”

Who are the New York Islanders?

400

This landmark in Queens is a giant stainless-steel sphere created for the 1964 World’s Fair

What is the Unisphere?

400

This LI town’s harbor was a major smuggling hub during Prohibition, supplying illegal liquor across NYC.

What is Freeport?
400

From Brooklyn’s Bed-Stuy, this hip-hop icon founded Roc-A-Fella Records.

Who is Jay Z?

400

This iconic hot dog brand has been served at Coney Island since 1916 and is the star of a famous July 4th eating contest.

What is Nathan's?

400

Originally founded in 1925, this NFL team played its early seasons at the Polo Grounds before moving to Yankee Stadium in 1956.

Who are the New York Giants?

500

This North Shore mansion in Huntington inspired F. Scott Fitzgerald’s “West Egg” and is one of the Gold Coast’s most famous estates.

What is Oheka Castle?

500

These two far eastern settlements were Long Island's first, coincidentally both starting with "South"

What are Southold and Southampton?

500

Born in Amityville and raised in Massapequa, this actor is the eldest of a famous group of brothers and is known for roles in 30 Rock and The Departed.

Who is Alec Baldwin?

500

This Long Island bakery brand—once based in Bay Shore—is known for crumb cake, donuts, and cookies sold in grocery stores everywhere.

What is Entenmann's?

500

This Mets pitcher threw the franchise’s first no-hitter in 2012—remarkably, 50 years after the team was founded.

Who is Johan Santana?