Hey M4,
Welcome up. I'll try to give you a few suggestions.
Maine:
Freeport-LL Beane's giant store. Nice shops
Bar Harbor-shops, Bed n' breakfasts etc.
Ogunquit is a nice beach/resort town. It is a bit touristy these days though.
New Hampshire-
Franconia notch is a beautiful area to drive through. The old man in the moutain was KIA as of this spring but, very scenic. Clark's trading post has bear shows and a small Zoo.I belive there is a flume and some beautiful trails as well. Sugar Hill Inn is a beautiful spot to stop for the night www.sugarhillinn.com
Lake Winnepesauke/Laconia/Weirs beach
There is an old paddle wheeler called the Mt. Washington that circles the lake. Arcades, restaurants, and also the site of a huge annual motorcycle rally.
Mt Washington.
Mountain that you can drive to the summit(if your car is reliable) and there is a small rail line when weather permits. Weather station at the top. stunning view.
Ruggles Mine:
Haven't been there in years but you could collect specimens and look for mineral deposits. Fun day with good hiking.
My experience in Vt is pretty poor so, I'll hope someone can pick up my slack.
hope that rambling helps some...enjoy the trip