First, Some Light Reading
Welcome aboard the RoadTrip America Forums!
You can see quite a bit of northern New England in a week long loop out of New York through POortland and Montpelier, and there is quite a lot to see. So what I'd first suggest you do is sit down with your travel partners and go over the discussions listed here, and of course the links therein. Then when you've all got a working list of the places that appeal most to you (and some wiggle room) we can work on finding the best and most scenic routes to connect them all.
AZBuck