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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

Newbury Berkshire UK 

A place situated in the South East of England, in the Thames Valley region.
Most inhabitants of this particular town claim to hate living here ... However, never seem to leave.

Most 17-25 year olds will, at some point have had a sexual experience with someone of the opposite sex who has also had a sexual experience with one or several of their friends and\or relatives.
Everyone in Newbury is in some way related to each other, suggesting some degree of inbred behaviour.
Being such a small town, rumours and gossip spread like wildfire, in short, everyone knows everybody else's business.
A high percentage of 17-25 year old males are either drug dealers, regularly sniff cocaine, ketamin, Meow meow and a high percentage of the females within this age range will at some point engage in a sexual act to gain such drugs.
I hate living in Newbury you can't take a shit without half of Newbury Berkshire UK
Newbury Berkshire UK by pinkdollymix September 25, 2014
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

the berkshires 

Located in western Massachusetts, The berkshires are a shitty place to live. There is nothing to do for teens but to have ragers in the woods. There are trees and mountains. The kids here are bitchy because they want to leave the valley. WE ALL WANT TO GTFO

kid: where do you live?
other kid: the berkshires
kid: THAT FUCKING SUCKS ASSHOLE!
other kid: i know
the berkshires by Travie D July 7, 2008

Berkshires 

("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."
Berkshires by Bill M. December 17, 2004

Berkshired 

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
Berkshired by Jhersch 20 March 10, 2011