So, the route is pretty much planned out and so is the calendar, but that still leaves a lot of things that need to be done, like what we do at certain places, things to bring, etc.

We could use some help, so if anyone could help us out with the following, we'd really appreciate it.

1. Tunes - We'll need quite a lot of tunes on our trip, since we're spending three full days in the car, so if anyone would like to send over some mixed CDs, we'll check 'em out and give you a shoutout, plus a little review.  You can either e-mail me playlists or mail me CDs to 7423 Ridge Blvd., Apt. 1B, Brooklyn, NY 11209.
2. Western NY - We need to stop in Western NY on our way to Cleveland and we got a tip that Olean, NY has a decent place to say and that pretty close to St. Bonaventure and Allegheny State Park, so that looks like a go to me, but we've set out to spend a fair bit of time trekking through Western NY the next day and would like suggestions on places to stop along the 86/90 route west of Olean.  I'm thinking food, farms, nature stuff...  quaint little places that no one knows about, etc.  It seems like it would be a pretty quaint country drive if we found some nice places to check out.  Also, if there's a place in the Olean, NY area that you think is worth staying at, let us know.
3. St. Louis - What to do in St. Louis on a Wednesday morning?  Brunch?  Shopping area?  Something historic?
4. Sioux Falls, SD - Where to eat lunch?
5. Yellowstone - Best place to camp out and also where to go to buy a lightweight tent for two without breaking the bank, since its probably the only time we'll need one.  We're going to spend  a day in Yellowstone. 

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.  :)