Clay,
In regards to riding groups, there is not a formal process to join a riding group. You will have to talk to others and initiate joining a group. Talk and meet people before hand, the evening before or the morning of and inquire where they are going and how they ride. If your not sure, find some of the AADs or Ron, our AD and we can steer you to a group. Many of us know each other and how they like to ride. Some ride 300 - 400 miles a day with their hair on fire, only stopping for fuel and eat Cliff Bars for lunch, other like to ride 150 - 250 miles at moderate pace and enjoy a nice lunch. No right or wrong, just different.
It may seem cliquish but it is not, you have to put your self out there and talk to people, we don't know if this is your first rally or not or if you just like to ride by your self. When approached, most will welcome you and tell you their plans for the riding day and how they like to ride.
RWTW is a lot of fun, you will meet lots of people from the SE and other regions, hope to see you in September.