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.