My step-sister lives in Bennington. It's overall a nice town. It's overall feel is "blue collar". She attended the school system and turned out OK

. At the time I was in school I chose not to attend the high school there as it did not have a good reputation-this was 20 years ago though, so I'm sure things have changed. I believe there is a catholic school for younger grades, but not for high school.
Bennington IMO has a "new york" feel vs. "new england" feel. It's news/weather outlets come out of Albany NY. Most people head that way for their major shopping as well.