KK, outstanding, simply outstanding. I have a few thoughts to toss into the hat.
Firstly, some years back, my uncle passed along to me one of the best pieces of business-type advice. He has been madly successful in business, so I asked him what would be the one piece of advice he would give me if he could only give me one. He thought for a few moments and then gave me his answer:
If you're planning any sort of venture, you'll discover that you need let's say five pieces in place before you can move ahead. Don't wait until you've got all five. Go when you get three and manage the other two.
That's my way of saying that things may not be perfect right now in terms of gas, the perfect equipment, etc.; however, you'll never go if you wait for things to be just right. It might help to do an assessment of what your venture needs so that you can better manage the things that are not as you might wish.
Secondly, I've only been up that way once and then just for a brief visit. On the other hand, the best vacation I ever took was in Vermont. My sweetie and I did the "random" tour of Vermont (this despite the fact that we had about 17 years combined residency there). Anyway, the rule was that the passenger got to choose the direction at each crossroad. We stopped for every roadside produce stand, sale, museum, etc. and had an adventure--mostly because of the people we met. I have traveled all over the US and a bit in Europe, but that trip is my most cherished.
My feeling is that the places you find are usually better than the places you plan. Follow Matt's advice and talk to the local farmers. Stop at all wayside spots. Eat at tiny, local diners, the kind where the waitresses still call you "honey." Ask them if there's a local pub or roadhouse that would like a band cheap for the night. Stay on the tertiary roads and leave lots of time for random stops. On the other hand, do hit recommended destinations as well.
I think it would be fun to watch the group enjoying the serendipity of meeting folks and making discoveries. If I were making it, which I am not, my passion would be to capture a warm adventure in a way that invites others to get off the highways and encourages them to have their own adventures.
Make it a journey.