I.B.
Hi C., I am from Wisconsin too and have a great friend with 2 boys in Pittsfield who could give you advice. I hate to post her info online but she owns the Stone School House Gallery and you can tell her her friend from Needham recommended you call. She would know the low-down on the schools as she is very thorough.
Good Luck.
As for me, I have 2 boys (ages 5 and 7) and both went to preschool. In many ways, I think it is more for the parents sometimes then the kids (Do you need a break?) Also, it was a very good socialization and early learning experience for them and has made other transitions much easier. Call my friend.