Four of us will be coming back to LI from Tanglewood a few times this summer. We'll have early breakfast up in Pittsfield, but I'd like to find someplace for lunch off of Rt 22 (time permitting, I prefer taking it over the Taconic).
I usually take 22 all the way down, and it's somewhere in that southern area that I'd like to stop: by then enough time will have elapsed since breakfast and a break will be nice.It doesn't have to be all the way down in Brewster, and it doesn't literally have to be on 22 (though I'd rather not take a 45 minute detour).
It should be a casual place but "interesting," and I'm pretty flexible with that. I can get plenty variety on LI so I'm hoping for something special (unique, quaint, or whatever). Not fancy-special but special to that area. Something like Red Rooster (though I've heard mixed things about how good the food actually is); one of the people with me will be elderly and if it's a hot day, as it might be in August, outdoor eating won't work (or, of course, if it's raining).
Last year on the way back I finally got a chance to eat at Big W's, and I was disappointed. The brisket looked *really* good but it was pretty dry. I'm not sure I want to give it another chance.
I personally don't really care for Italian food, but I'm more or less open to pretty much anything else.