OP here! Thank you for all of the suggestions so far! I am getting ready to print the thread to this point and make notes of all the suggestions!
In answer to an earlier question, we DO plan on doing Deerfield and are planning to swing up into Vermont from that point.
So, basically flying into Boston, seeing as much as we can there and hopefully catching a Sox game, then out west to Deerfield and north into Vermont, New Hampshire and on to the Maine coast.
Anyone have anything specific to recommend seeing or doing in Vermont and New Hampshire? Or just a pleasant driving route across them?
Thanks again for the suggestions and by all means keep them coming!