Well, I haven't given up on what I tried last year. My basic legal hurdle was the insurance. In my state, to do anything in the public (be it race, picnic, or even a speech) you have to come up with at minimum $1,000,000 insurance policy to cover the event if it's going to be via any public parks, property, etc. Last year, I tried to setup such an event on the Natchez Trace Parkway, because it has no stoplights, it has low speed limits (50MPH and under) and a good variety of scenery that in itself makes for a great ride. That and excellent road conditions. But, after spending half a year search, I couldn't find any insurance company that would cover it. I finally contacted the Parks Commission about this and said "hey, no one will insurance this, so how is everyone else doing it?" and they referred me to a insurance company in Illinois. I talked with the guy in charge and was about to get everything done when at the last week, somehow all the paperwork got lost. The parks people didn't have any proof of insurance and thus would not allow event. The insurance company lost the guy that was handling my case (as in he quit to go work somewhere else) and it came tumbling down, so I just had to cancel everything.
This year is different as I'm going to exploit a loophole. At the very end of Natchez Trace is a small area that has a gas station, restaurant and a fairly medium sized motel. (Called the famous Loveless Cafe & Motel) http://www.lovelesscafe.com/
I've been talking with the owner and he's up for an e-bike event. Basically, we can use his parking lot as the starting point, and then go on to the Natchez Trace (which is a easy "merge onto the trace" entry point, no delay, no stoplight, no needing to cross traffic, just merge right on the start of the Trace) at which the event can continue from there. If all goes well, not only can one stay at a cheap motel before the event, you'll be right there in the morning when it begins. But I didn't want to get all the cheer about this out until everything was truly final and I could present everyone a solid "it will happen on this date/time, to go ahead and plan for it" kind of announcement.
This gets me away from the "you gotta have $1M insurance and a mountain load of paperwork" if I did this directly on the Natchez Trace vs. starting it somewhere else and just having it continue on it from there.
Once I pass that hurdle, then it opens up many miles of roadway and "rest stop" areas every few miles that we can use for whatever our imaginations can think of that might make it an interesting e-bike convention of sorts. That's also why I've bookmarked the "racing" topic started in the general discussion area