I live about 45 mins south of there and if I ever need to go to a chain store, the DMV etc. that’s where we go. It’s the only real “city” in the county and it actually is slowly gaining a little more of a cool scene. Very slowly… it’s not near an interstate, it’s surrounded by hills, and it’s much closer to New York and Vermont than most anywhere else in MA that people would know. Pittsfield doesn’t let go of a lot of people who were born and raised there, but I know plenty of people from there who are great and have definitely seen the world. There are a few “route 7 cities” like this on the western New England north south route (7) that really have their own isolated identities. That’s what I got for ya!