(NOTE: A I was composing this, another post was made with some thoughts echoing my own... all groovy, man!)
Wow!

I can't believe how much feedback I've gotten so fast from my one tiny idea!

My original musings n this are now at least five or six years old at east. I suppose my inspirations were drawn from folk-jam events I've seen over the years, as well as an old PBS show centered around the bluegrass fests at Ashokan, NY and Woodstock, VT. The central idea being for a daytime event, possibly featuring a headliner act or two at a main stage for the crowds, but with enough accommodations for musicians and the hardiest of patrons to remain overnight, thus facilitating a (STRICTLY acoustic} "campfire jam" that would last as long into the night as the bravest could handle.
Of course, as this vision solidified, the concept of taking the train to the music quickly followed. After reading the thoughts expressed above, as well as my own applied reality, I now see that as a far-term goal after several (5 or so) years of "seeding" the event.
I can now easily envision a twofold event with the main focus starting at Sheepscot, (at least to start with) and including some augmentation of entertainment at Alna Ctr for those taking the train- much as many of the current events do now. This has one advantage in particular, it gives folks another place to go and hang out, thus keeping crowds from getting too crazy in either one location.
So my suggestion for now is to allow for overnight/camping on RR property at A.C for musicians (mostly) and a campfire event there, like the ones at Christmas time. (Perhaps some of the musicians can be recruited to return for that event as well!

) Then there follows the idea that musicians camping there can take an early shuttle train down to Sheepscot for the event there while others are "warming up" at AC. If the musicians all, mostly camp at AC, this frees up parking for more guests at Sheepscot.
I would suggest to begin with a one day event with some limited camping allowed (on about the level of our current work weekends) to see how well it works, and to implement other ideas on small scale basisies over the interim with the ultimate goal being for a two-day event with fully half the action at Sheepscot and half at AC, and with somewhat modest accommodations for camping, mostly for musicians and volunteers, but for some patrons as well (although I'd suggest keeping patron camping limited- if only to keep the event from exploding out of of control.)
Whatever happens and however it unfolds, I am confident that the human and material resources to make it happen are already present in our organization, and that the right frame of mind exists to make it, as Maude Lebowski says: "...a natural and zesty experience."
To end with anther movie quote, this time from Kelly's Heroes: "Hey, so many positive waves, maybe we can't loose!"