This sounds like a lot of fun. I didn't get my TJ until mid October, but this kind of thing is very much something I'd be interested in in 2011. I'll have to keep my ear to the ground for other such opportunities.
I have been driving my 98 Jeep Cherokee Classic for about a couple years now and I've fallen in love with all things Jeep. A Jeep ride close by (like Bowling Green) would be a wonderful way to meet other Jeep lovers in the area. Whoever is in charge of this sort of event I would love a message from them on here. Thanks.