Top Definition
("BURK - sheerz") The western half of Massachusetts. Pretty much everything west of Springfield, regardless of whether or not the town is in the actual county of Berkshire. Known for its heavily wooded areas, ski resorts, and small towns, in contrast to the more urbanized eastern half of the state.
"We went to the Berkshires last winter to go skiing."
by Bill M. December 17, 2004

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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
by mobius131186 June 15, 2005

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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.
by KCP May 01, 2005

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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!
by bostonbabe174 May 07, 2005

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The prep school that once was great but now has turned into Taftshire under the mountain.
All these new people from Taft
by Harriot May 05, 2005

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Classiest mofing place on the planet, full of bra less druggies and cats!
BERKSHIREEEEEE! booty
by CatMonkeyLion January 06, 2012

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(v.)to stab someone with the No. 1 drafting pencil in America, the Pentel(R) Sharp™ Automatic Drafting Pencil
If you don't stop talking, I'ma berkshire your ass.
by Ice Cool November 04, 2007

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