Berkshires vs. Pioneer Valley
Like some of the other posters, I recommend the Pioneer Valley towns rather than the Berkshires proper. The Valley has lots of people interested in organic gardening, ecology, yoga, alternative medicine, etc. I am most familiar with Easthampton and the Florence part of Northampton. They are the kind of family-safe areas where kids can play outside most of the year.
The only reservation is that I think the public schools are more in the range of average-to-mediocre rather than great. There are some good parochial schools and private schools. If "great" public schools are a priority, you might look at the well-financed suburban areas like Columbia, Maryland, New Trier, Illinois, etc.
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