Roadtrippin'... Driving across the country in July and the app that could have helped me

I'm not much of a traveller, I'll admit that.  I can count the number of times I've been out of the country on one hand, and one of those times was Canada, so I'm not entirely sure that counts.  (Just a little good clean Canadian humor, eh... just kidding around.)

So, when the idea of a cross country road trip was proposed to me, I jumped at the idea.  Ok, so actually, I thought about it carefully, and created several maps and spreadsheets on it, but the jumping was there in spirit.

But, actually, the whole planning thing was not only a logistical pain in the butt, but I thought of lots of opportunities for web app to help me out.

So first off, here's the trip:  (PS... All these yellow markets aren't necessarily real stops... sometimes, I just had to make sure Google Maps put me on the right road so I had to enter somewhere random to force it.)

And here's a link to the real map...   

And then to our calendar.    It's quite ambitious...  and no, I'm not driving the 'Stang.  No interest in putting 4900 miles on it.  That's what rental cars are for.  Plus, we're only driving one way.

But what I really wanted was a great integration of a map and a calendar, one that took into consideration driving times.   On top of that, I wanted to layer on events and hotels... ones that took into consideration the time I was going to be there.  For example, by random chance, I stumbled upon a fair in St. Louis going on right around July 4th when I'm going to be there.  Also, it was a pretty manual process to match my driving and my calendar with the various baseball games that I wanted to see, because teams aren't always in town when you are.

Not only that, the group collaboration around this trip was very manual... mostly with passing links back and forth.   I wanted to give my co-pilot the opportunity to comment on various parts of the trip.   Plus, the collected wisdom of others came in handy.  We got advice from others to make sure we hit the South Dakota Badlands and exactly what time to hit them.  Now we know that, but what about others making that same trip.

So what I'm looking for is a Google Maps, Gcal, Travelocity, Yelp, Gchat, Wiki, Blogs, Flickr mashup for roadtrips.   That doesn't seem like it would be that hard to do.  :)