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1.) In reference to Berkshire County, Massachusetts, known for its quaint small towns and unusually high cultural-attractions-to-people ratio.
2.) Exorbitant classiness or sophistication, often when such sophistication is unexpected.
Friend #1: Bro, I'm gunna slide into the DM's today!
Friend #2: I too will slide into the DM's but using an appropriate semicolon; I'm no savage.
Friend #1: Dude, that's berkshire.
berkshire by wx413 January 9, 2019
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A county in Southern England, bordered by Oxfordshire, Hampshire, Surrey, Buckinghamshire and Wiltshire. Its principal city is Reading, known for its annual rock festival.
Reading is a town in Berkshire
berkshire by mobius131186 July 15, 2008
aka Bakeshire! Prep school hidden under a majestic mountain where boys and girls in wornout t-shirts and khaki shorts play lax on the quad with out a care in the world.
Berkshire is a great place to go to high school.
berkshire by KCP May 1, 2005
A prep school that is in Massachusetts. Some students call Berkshire, Taftshire due to the influx of faculty from the Taft School. Berkshire is a fun place.
Holy crap, is that new teacher from Taft too?!

YEA DUDE HE IS!

Wow, Berkshire is really Taftshire!
berkshire by bostonbabe174 May 7, 2005
Berkshire is where lads are from. It’s a place where the lads can get pissed and have an annual festival in Reading. Berkshire is also home to the mighty Ding and shit over all the teams in the EFL and have the biggest firm in the country.
P1: “Oi where do u wanna go tonight”
P2: “Lets go to Berkshire it’s the English Ibiza”
Berkshire by Take it easy September 28, 2019
The prep school that once was great but now has turned into Taftshire under the mountain.
All these new people from Taft
berkshire by Harriot May 5, 2005
Fuck off Swindon sheep-shagger, Berkshire is civilised.
Berkshire by Dibber April 19, 2005