I know im an out of stater, but i spent time in Bennington and the problems the town has seems pretty clear to see:
No job range of any kind - you're either a research scientist for Plasan, or you're college educated and working at Freindly's. With a jobs picture like that, Bennington shouldn't be surprised that they are stagnant. If a family can't find cost of living employment, then what kind of people do you expect will move into the area? From what I've seen, Bennigton has the least amount of opportunity to work than in any other place in Vermont.(okay,okay - you're ahead of North Hero and Island Pond).
You can build all the bypasses you like, but if your connection to NY or anywhere else are little more than cowpaths - you're cut off, economically isolated. Shoulda spent that bypass money to work with NY to improve route 7 to connect Bennington to the NY Capital District.
I don't know why many of us stay here.....
The State of VT (and the feds are making it more expensive with associated taxes) makes it very difficult to be in any kind of business. The hoops that has to be jumped thru to start or expand a business here is mind boggling. One of them is building a sidewalk that no one will use. Many have left.
Bennington has become and remains to be a bedroom community to mASS and NY. The number of cars with green plates heading south and west in the morning is alarming. But that is where the decent paying jobs are.
The town's leaders thinks it's great when almost all of the stores in town are occupied. Only to see some of them close a few months later due to few sales. Service jobs do not pay all the bills. Service jobs does not allow one to shop on Main St..
Our kids more out, welfare moves in.