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.
by wx413 January 9, 2019
A county in Southern England, bordered by Oxfordshire, Hampshire, Surrey, Buckinghamshire and Wiltshire. Its principal city is Reading, known for its annual rock festival.
by mobius131186 June 15, 2005
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 2, 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!
by bostonbabe174 May 7, 2005
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 5, 2005
Bershired is when a person or organization takes advantage of families who have children with disabilities. They offer false hope and rob people of large sums of money
The Center Berkshired my parents into spending thousands of dollars for supports that did not exist
by Jhersch 20 February 24, 2011
("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