The Berkshires is a mountain range in Western MA. It is not a city per se. Western MA is more akin to CT or VT than it is to the central and Eastern part of the state
of Taxachu...I mean MASSachusetts.
MA really begins East of Springfield, around Worcester & the route 495 and 290 region, too. The State House in Boston has no conception of Western MA, they figure it's the sticks despite the fact that UMASS is out there...but they sure as hell will take the tax money.
The nicer cities in the Berkshires may be Lee and Stockbridge for running, but in some of the rural areas it's pure "Deliverance" mindset in a number of locations: lovers of NASCAR, country music, many pickup trucks, applliances on porches and at least one Horrific anti-pro-choice billboard, which I myself saw and was appalled by.
Also be aware that the Kennedy's are NOT universally loved up here.
And so ends this public service bulletin.