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100

This Cambridge-raised duo grew up as childhood best friends before taking home the Academy Award for Best Original Screenplay for 1997's Good Will Hunting.

Who are Matt Damon & Ben Affleck?

100

Popularized by Boston Globe sportswriter Dan Shaughnessy in a 1990 book, this superstitious moniker explained the Red Sox's 86-year World Series championship drought.

What is the Curse of the Bambino?

100

Starting at Boston Common and marked by a red line on the sidewalk, this famous 2.5-mile walking route leads visitors past 16 historic Revolutionary War sites.


What is the Freedom Trail?

100

Unlike its Manhattan counterpart which uses a red tomato base, New England style clam chowder is famous for using this rich ingredient as its liquid base.

What is cream (or milk)?

100

Running directly beneath the streets connecting Boston and Cambridge, this university system operates the largest academic library collection in the world, holding over 20 million volumes.

What is Harvard University?

200

Born in Boston in 1970, this actress became a Quentin Tarantino favorite after starring in Pulp Fiction and playing "The Bride" in Kill Bill.

Who is Uma Thurman?

200

Every Patriot's Day, thousands of runners line up in Hopkinton to tackle "Heartbreak Hill" and finish in Copley Square during this world-famous event.

What is the Boston Marathon?

200

Protesting the "Taxation Without Representation" imposed by the Tea Act, the Sons of Liberty dumped 342 chests of East India Company tea into Boston Harbor on December 16, 1773, in this famous political protest.

What is the Boston Tea Party?

200

Founded in Quincy, MA in 1950 by William Rosenberg, this fast-food coffee and donut giant is an essential part of daily life for most New Englanders.

What is Dunkin' (or Dunkin' Donuts)?

200

Downtown Boston’s green Rose Kennedy Greenway exists today because this massive, 16-year mega-infrastructure project replaced an ugly elevated highway with underground tunnels.

What is the Big Dig?

300

Born in Brookline, Massachusetts, this 35th U.S. President was the youngest person ever elected to the office and famously delivered his inaugural address urging citizens to "ask not what your country can do for you.

Who is John F. Kennedy?

300

While every other team in the NBA plays on court surfaces made of hard maple, the Celtics' parquet floor at TD Garden is uniquely built out of this type of wood.

What is Red Oak?

300

Local folklore claims you can still smell sweet syrup in the North End on hot summer days as a reminder of this tragic 1919 industrial disaster that killed 21 people and injured over 150.

What is the Great Molasses Flood?

300

Created in 1856 by chef Chef Raulin at the Omni Parker House on Tremont Street, this chocolate-glazed, custard-filled treat remains the official state dessert of Massachusetts.

What is Boston Cream Pie?

300

Unlike most U.S. cities, you won't find discounted after-work drink specials in Boston because Massachusetts passed a statewide ban on this promotion in 1984.

What is Happy Hour?

400

Known as "The Splendid Splinter," this legendary Red Sox left fielder was the last Major League Baseball player to hit over .400 in a single season (.406 in 1941).

Who is Ted Williams?

400

At its base, this famous 37-foot wall houses one of the last remaining manually operated scoreboards in Major League Baseball, updated from the inside by hand.

What is the Green Monster?

400

Among the 13 works stolen during the 1990 heist at Boston's Isabella Stewart Gardner Museum was The Concert, one of only ~34 surviving paintings by this 17th-century Dutch master best known for Girl with a Pearl Earring.

Who is Johannes Vermeer?

400

Tourists and locals routinely wait in massive lines on Hanover Street in the North End to settle the score in a fierce rivalry between Mike’s Pastry and Modern Pastry for this classic Italian crispy shell dessert.

What is a cannoli?

400

Equal to 5 feet 7 inches, this non-standard unit of measurement was created in 1958 by MIT fraternity pledges to measure the length of the Harvard Bridge.

What is a Smoot?

500

This Founding Father organized the Boston Tea Party, signed the Declaration of Independence, and is now best known to modern Americans as a namesake Boston lager.

Who is Samuel Adams?

500

To prepare for his role as a South Boston police officer in 2006's The Departed, this actor spent months riding around in police cruisers with real Boston beat cops and studying local speech patterns.

Who is Leonardo DiCaprio?

500

Taking their name from a speech delivered in the British Parliament by Isaac Barré, this radical group of Boston patriots operated out of a distillery and rallied behind the slogan "Taxation without Representation is Tyranny."

Who are the Sons of Liberty?

500

Invented in Somerville, MA in 1917, Marshmallow Fluff is combined with peanut butter between two slices of white bread to make this official state sandwich of Massachusetts.

What is a Fluffernutter?


500

Every year on October 16, MGH celebrates "Ether Day" to mark the 1846 demonstration that eliminated pain from surgery, giving birth to this medical specialty.

What is anesthesiology?