I did the reverse about a 2 years ago... started in WV, went west on the northern route, east on a southern route.
If you're into camping / hiking, go through the SD badlands, and the Black hills. check out Mt. Rushmore and the indian thing (Crazy horse?) both are worth a few days if you can spend it there (camping's cheap - GREAT parks in the black hills). Yellowstone is a must at least once in your life but spend at least 3 - 4 days to see the fun stuff.
Chi-town is always a blast - go see a Cubs game and have some good steaks or pizza. Indiana and Ohio suck though. If you go through Dayton, you HAVE to stop at the flight museum at Wright / Patterson AFB. Be sure to take the bus out to the other building to see the X-70 Valkarie and the other planes they keep hidden back there.
PA is pretty boring too, but if you drive through, take pictures of yourself standing in front of all of the towns with goofy names (Intercourse, Beaver College, Blue Balls, etc.). Jersey rocks. Stop by the Rutgers - New Brunswick Campus and eat a Fat B*tch at the Grease Tucks on College Ave. It'll be the best sandwich you'll ever eat (although now the PC police have changed the name to a 'fat beach'
There's always NYC if you're going that far north. Stop to see the Twin Towers site. Southern Jersey has Six-Flags Great adventure. Philly has LOTS to do including 'Midnight Floyd' at the planetarium.
DC is a must. I particularly like the Smithsonian and the Library of Congress. Stop by your Senator's office if he / she's in and ask if one of the aids can give you a brief tour - you might get to sit in the peanut gallery above the senate for a while. Make sure to call ahead though and explain what you're doing - suggest what you want to do otherwise, you'll be blown off quicker than a freshman at rush.
If you're going further south, there's always Vegas and the surrounding stuff down there. Not much from there East though unless you drop down to Dallas or even further south. Pretty much from Vegas to Tennessee is a long boring drive, lots of flatness and in AR, the roads are a b*tch.
Oh, and in case you werent watching the news, stay away from I 10 unless you wanna go swimming.
I guess that about covers it. stop by a AAA office - they can plan everything out for you - then they give you free books and maps to boot.
Good luck,
Texan