Winchester
Pop Culture
Win Government
2025
2025
100

Established in 1902, the En Ka society originally began as this type of group.

What is a sorority

100

Which band’s concert kiss-cam exposed an affair between a CEO and the company’s chief people officer?

Coldplay

100

Winchester sits in this number Massachusetts congressional district

What is the 5th
100

Which world famous art gallery was robbed in October this year?

The Louvre

100

What is a Labubu

Stuffed Animal

200

The original 1896 town seal of Winchester includes this other land grant name from 1638.

What is Waterfield.

200

Which 90s rock band reunited for a tour and held their first performance since 2009?

Oasis

200

Winchester's congressional representative

Catherine M. Clarke

200

Who was elected as the mayor of New York City on November 5?

Zohran Mamdani.

200

Actress Sydney Sweeney did a jean ad that many found controversial and problematic for what brand?

American Eagle

300

The town of Winchester was incorporated in this year.

What is 1850

300

Following the death of Pope Francis, who was named the new leader of the Catholic church in May this year?

Pope Leo XIV

300

A select board of this many members oversees town operations

What is 5

300

What did the Oxford University Press name as their word of the year?

Rage Bait

300

What famous comedy show celebrated their 50th anniversary?

SNL

400

this decade saw the first En Ka street fair

what is the 1930's (1932 to be exact)

400

When going to collect his Oscar for his role in the Brutalist, what did Adrien Brody throw at his girlfriend Georgina Chapman?

What is his chewing gum.

400

Winchester's official "sister city" is in this country

What is France (St. Germain en-laye)

400

Who won album of the year at the 2026 grammies?

Bad Bunny: Benito Antonio Martínez Ocasio

400

Charlie XCX made headlines in 2025 for what reason?

Getting Married

500

Named in 1961, this is the oldest one of the current five elementary schools - not in building necessarily, but in name.

What is Vinson-Owen.
500

Which budget airline’s advertising slogan went viral on TikTok earlier this year?

Answer: Jet2, with the phrase “nothing beats a Jet2 holiday.”

500

Winchester was almost named this ...

What is Columbus.

500

Justin Beiber went viral in 2025 for what phrase?

It's not clocking to you

500

What unexpected event did Harry Styles secretly complete in 2025?

two marathons