Very interesting Peter,
My son's coming home so maybe we'll take a ride this weekend.
There's a lot of good food in the Berkshires (NY and Boston Summer and second home people). It's a little far from my place so I don't get out there very often.
Hudson, NY was a very down and out city not all that long ago but it's main street is now filled with antique stores, art galleries and good restaurants including the best Mexican around here, Mexican Radio http://www.mexrad.com/
There hasn't been that much trickle down but a lot of New Yorkers are moving up this way.
You can take the Train from Penn station and be in Hudson in a bit over two hours. If we had a "real" train the trip would be less than an hour. I suppose I should be careful what I wish for.