history
tv & film
pioneer valley geography & one that isn't pioneer valley specific
art & music
pop culture
100

Born just a few years apart in neighboring Massachusetts towns (Springfield & Holyoke), these two sports both got their start in Massachusetts YMCAs.

What is Basketball & Volleyball?
100

This Louisa May Alcott’s tale of three sisters, based and written in Concord, MA, has been adapted into movies and TV shows many times—most famously in 1994 and 2019.

What is Little Women?

100

This Massachusetts college town, nicknamed "Lesbianville, USA," has an official slogan that states "where the coffee is strong and so are the women".

What is Northampton, MA?

100

Huckle Cat, Lowly Worm, and Sprout Goat are some of the various characters who can be found within the busy world of what Massachusetts-born author and illustrator?

What is Richard Scarry?

100

Found in countless lunchboxes, this fiber-packed cookie takes its name from a Boston suburb.

What is Fig Newtons?

200

In 1897, Boston became the first U.S. city with this type of public transportation system.

What is the subway system?
200

In this Massachusetts-set TV show, a teen witch balances homework, magic spells, and advice from her weird aunts. Also, the name of a banger DJ/producer.

What is Sabrina the Teenage Witch?

200

Most MA town signs share this everyday object shape.

What is Book?

200

This Boston native claims the Berkshires his home after spending time in the late 60s at the Austen Riggs Center of Stockbridge treating his heroin addiction. He references the "turnpike from Stockbridge to Boston" in his music. 

What is James Taylor?

200

Founded in the Pioneer Valley and the North Shore, these companies turned wax and wick into a multi-scented empire.

What are Yankee Candle & Kringle Candle?

300

Visitors to this Massachusetts site can watch actors reenact 17th-century colonial life, from blacksmithing to traditional farming. Great place to buy giant gobstoppers too.

What is "Plimoth" Plantation (Plymouth)?

300

“Where everybody knows your name” — this Boston bar became the setting for one of the most beloved sitcoms of the 1980s and 1990s.

What is Cheers?

300

This Pioneer Valley town is said to have inspired Whoville, and each year locals celebrate it with a “Holiday Whobalation,” singing around a tree in true Seussian spirit.

What is Easthampton?

300

Famous writer Henry David Thoreau spent two years in solitude near what pond in Concord, Massachusetts, which also serves as the name of the book he wrote about his experiences there?

What is Walden Pond?

300

This tongue-in-cheek term is often used to describe a stereotypical driver from Massachusetts.

What is Masshole?

400

The chocolate chip cookie was invented in 1938 by Ruth Wakefield, the proprietor of what Massachusetts inn, which gave its name to the Nestlé brand and cookbook that popularized them?

What is The Toll House Inn?
400

Set in Boston and starring Matt Damon this film won Best Original Screenplay at the 1997 Oscars.

What is Good Will Hunting?

400

This Northampton dive bar features one of the only public beer can museum's with over 4,000 historical and novelty beer cans, including some of the oldest in American history. Anna and Iris have both been here.

What is Ye Ol' Watering Hole?

400

This comic book, and later tv series, franchise was created in MA town Northampton back in 1984. In 2023 the town even installed several custom manhole covers honoring the sewer-dwelling heroes.

What are the Teenage Mutant Ninja Turtles?

400

This is the birthplace of both Dunkin Donuts & Miss Sophia Rose Gill. Also, the middle name of a certain US president...

What is Quincy?

500

In 1919, a giant storage tank burst in Boston’s North End, sending a sticky wave of this substance through the streets.

What is Molasses / The Great Molasses Flood of 1919?

500

This Boston-area TV show has been highlighting New England restaurants, diners, and other food related gems since 1993. It is NOT as good as ABC's The Chew.

What is Phantom Gourmet?

500

This rural town has a slightly suggestive name, hosting the Massachusetts Sheep & Woolcraft Fair (where Penny Gill won Best in Show for her needle felting...), and is known as a haven for artists and writers.

What is Cummington?

500

In 1990, thieves disguised as police officers stole 13 pieces of art during the biggest art heist in U.S. history—the works have never been recovered.

What is the Isabella Stewart Gardner Museum?

500

A die-hard Boston Red Sox fan, this actor reportedly refused to wear a Yankees cap in a New York airport scene in Gone Girl, forcing production to compromise with a Mets hat instead.

What is Ben Affleck?

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