As a real estate professional, you know we can't really speak to the quality of schools in the area. There are a lot of sites with that information.
As far as areas with good resale values, I like both Pownal and Shaftsbury in the Bennington area. Pownal is south of Bennington and Shaftsbury is north.
Pownal is close to Williamstown, MA and the college there, so it can carry values well as an alternative to the home expenses in northwestern MA.
Shaftsbury, being north of Bennington is closer to Arlington and Manchester and the high property values there.
Both towns are more rural with a mixture of large acreage properties and some areas of higher density. I can't speak to local events in either town, but I know that Bennington has events on a more regular basis and is a short commute from either town.
Hopefully that will give you a starting point.... more