Planning First Off Road Trip

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uchoops4

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So after a whole lot of talking, and very little planning a group of friends and I have decided to take our first off road trip this summer. A group of of six will take three jeeps and head out on the Trans American Trail. We are planning on starting on the West Virginia portion of the trail, from the starting point in Ripley, WV. We will head through W.V., into Virginia and hopefully end our trip in Tennessee. We are planning on having three full days of driving, a 5 day trip over all. So I have tons of questions, but will start with the first. What is the best road to go for planning such a trip. I have looked at the videos I can find and it looks like this portion of the trail is fairly easy to navigate. Could I be wrong? Anyway as we start planning (we are officially 3 months away) any information is appreciated.
 
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