Here's what I've learned from the Bennington Bash round 2...
Having multiple route options for the big ride day is nice. It's hard to herd 100+ bikes to one place! And after about the first 20 bikes, it's hardly spirited riding anyway.
We published route maps. It was helpful for some people, but there were also LOTS of cops out there, it's almost like they had access to the route maps!!

The main hotel near the camping would have been nice... It was an 8 mile ride into town from the camp for us.