Not right in town but worth the short drive for a great dinner is Tourterelle (
French Country Restaurant | Middlebury Inns | VT Organic Restaurant ). We had an absolutely delightful dinner there over fall family weekend and will definitely plan on going back. A real hub is American flatbread. It was packed family weekend, but again, really good. I will also say that 51 main was a great spot for meeting up and catching lunch, dinner, etc. Owned and run by the college, it is a great spot in the heart of the downtown area.