Surreal restaurant/music venue deep in the Berkshire hills with an improvisational, O.G. hippie vibe which transports you deep into a late 60s/early 70s post-Woodstock house party (including the unpredictable quality of the food). N.B.: closed annually for the winter but good luck finding the opening dates. (Also technically not in upstate NY, but a winding hour-long drive is de rigeur for doing most things in this region)
One of my favorite places in New York. Artists doing weird shit for cheap, it’s freaky, it’s inspiring, it’s accessible. Last time I was there I watched a girl sing all of Hamilton naked drinking wine <3