Just seeing this thread now. Kevin and I are going to start talking about possible locations in the near future. My GF's dad has contacts at Lime Rock Race Park in Lakeville, CT and at Stafford Speedway in Stafford Springs, CT.
Ideally I would like to do this at Lime Rock. They have camp grounds in the park, so I though it might be pretty sweet if we camped out there for the weekend, had a cruise through the hills of Western, CT/Eastern NY, and then have our car show in the infield of the track. I though about possibly organizing a track day on Saturday as opposed to the cruise, but that would probably be crazy expensive (track day costs can range from $200 up to $400 per person depending upon how many people commit).
I have to put down on paper what we want to do so I can forward it to my GF's dad so that he can see if it's possible. The owner of my company is also friends with Skip Barber so I might have a little pull there as well because he has a school at the track.
Right now things a still really up in the air, but I'm going to try and coordinate with Kevin soon so we can get the ball rolling on this, I've just been really busy over the past four weeks.
We'll update when we know more.