It seems to me to be not dissimilar to the Adventure that Bill and I had (seems odd to say this now) LAST YEAR. Perhaps it would be helpful for you to know a little about how it was accomplished.
I began by mapping out a tentative route (which was later changed radically) that would pass through places I knew some 'Catters lived. I sent some emails to the people I hoped to visit, asking how they would feel about the possibility of having a 'Catter or three appear on their doorsteps. After receiving some tentative but positive responses, I began planning the route with greater definition. I sent a few more emails to those whom I knew lived along the new route. More positive responses and more adjustments were made to the route. This route/itinerary was posted in a thread along with a probable starting date and a request for more 'Catters to let me know if the route was passing somewhere near their cities. A zillion emails later, I finalized the route and the plans for departure. Then I had a brainstorm about doing a "hit the road" show at a local coffeehouse and made arrangements for that as well.
Among the deciding factors for the direction of the route I chose was the hope of being somewhere near certain areas when festivals such as Old Songs and the Wyoming Cultural Fest were taking place. There were other events such as the monthly meeting of the Oklahoma City Traditional Music Association that we wanted to be around for as well.
The hard part was that I was only able to be away from my job for a certain amount of time. For that reason Bill and I had to absolutely RACE from one stopping point to another in order to complete the route on time. Another part of the planning involved making certain that we usually didn't travel more than three or four hundred miles in any one day. (Ha!) Yet another part was ensuring that there were accommodations of some sort at each potential stop. This involved a multitude of hotel reservations for which I managed to acquire a number of discount deals.
The planning for all of this required a whole lot more effort and time than can easily be imagined. In the two months before we launched the Adventure, I received and sent an average of six PM's and two emails each day. There were countless phone calls (many of them long distance) as well.
I hope that by knowing some of what I did you will get some idea of where to begin. I won't say that I chose the very best methods for accomplishing my goals, but they worked (or Bill and I and various Mudcatters MADE them work!). It is because of the success of the Adventure, that I have every faith that the Roadshow can become a reality.