Connecticut is good in the Fall, and that's it.
Here are my suggestions:
Watch Hill, RI
Somerset PA (Amish country, lots of cheap accomodations, and the 9/11 plane memorial at the actual crash site)
Keene NH (Good food at Don & Daves Wings and in Troy Gap Mountain Breads) Camping is good. Hotels suck. College girls. High lesbian concentration.
Wind Generation fields of Kansas / Missouri / Utah / Arizona
Colorado. All over that state. Spend like, 3 weeks there you'll always find things to do.
Drive through Iowa at sunrise.
Mystic CT / Newport RI
Niagara Falls. Go into CA too.
Napa Valley, CA
That winding road that Martine takes down in Virginia.
Elephant Butte, New Mexico
Roswell NM
If you go across the central states, the southern route (73 I think) has more things on it to do, but the northern route (Through Chicago) is more interesting to look at. It's also how you go through Iowa.
-> Steve