It looks like Mark has answered your second question, so let me take a stab at your first. I would say the highlights of your trip might include some of the following:
Cataract Falls south of Cloverdale, IN.
The museum at the Indianapolis Motor Speedway
Octagon Mounds just west of Newark, OH
Falling Water south of Donegal, PA
Old Bedford Village in the city of the same name (PA)
Hershey Park in PA
Caves in PA: Indian Echo Caverns and Crystal Cave
Mystic Seaport in Mystic, CN
On a separate note, I will point out that the direct route will take you right through the heart of New York City and that some can find this daunting, to say the least. If you would rather avoid this, there are ways around it, but what to do about getting through or by NYC is something that you should consider beforehand.
AZBuck