That's a hard no.
20 miles - about 30 minutes. Directions --> https://goo.gl/maps/nj268KPy959C4ivU9
Yes, there will be charcuterie offerings with cocktail hour, followed by wood-fired brick oven pizzas by Truckin' Pizza, and late night snacks.
Obv. The Roaming Speakeasy will be serving up a selection of domestic beers, wine, and batch cocktails.
Depends on your skill level, but the terrain is lawn, and dirt/sand.
Yes, it will be a blubbering-fest.
It's Maine - be prepared for anything. But generally, daytime temperatures can range from 60s-70s. We recommend bringing layers for the evening.