Thanks guys for the helpful suggestions. To Dave's point. Here is what we like to do We are three guys who went to college together a long time ago. We have spent most of our time after that in cities (me in NYC, my friends in San Francisco). We want to see a part of America city slickers don't get to go to. That's the main priority. Other things we like (or at least one or two of us do :)) is a good drink, a good piece of barbecued meat, a good conversation.

Seems from your advises (and a few things I have been looking into), we can pick up some good routes to drive uptill halfway point . Be it I70, or going up to Yellowstone and coming back down via the Dakotas. Problem is that after the halfway point scenery seems to settle down and it's a mad rush to get to NYC. Any suggestions on what routes we could take say beginning of midwest to new york?