Rockport sounds nice, but it is a pretty big drive to get out there.
I checked MapQuest and these are the distances to the major places around here (and moab). I haven't been to most of these places, but Disney isn't as far as I thought.
Joplin, MO 74 mi
Disney, OK 136 mi
Potosi, MO 178 mi
Hot Springs, AR 261 mi
Rockport, IL 282 mi
Moab, UT 1122 mi
I think it would be great to have a planned run to Disney or somewhere a little more challenging and further away once or twice a year. Not everybody will be able to make it, but we will keep on doing the more local runs in between which will be more convenient for everybody.