RE: Rt. 8 & Rt. 20, upstate CT/Western MA
Are you looking for laid-back or upscale? There's not a ton of great restaurants on the way from Winsted to Otis. My family lives a few miles outside of Winsted, but luckily, my stepmother cooks like a pro, so we never ate out around town that much.
That said, however, there are some decent pizza places in Winsted. If you're willing to make a brief detour, there's a fantastic little restaurant in Torrington, CT (right next door to Winsted) called The Galapagos Cafe. It's in a little building on a quiet road a few blocks away from the center of town. Breakfast all day, homemade bread, fantastic seafood dishes, great soups, etc. The last time I was there, I had an amazing paella. My husband, who doesn't like seafood, made a meal of their homemade black bean soup and a basketful of hot bread, which reminded him of the bread he ate growing up in Puerto Rico. The people that run it are lovely, too. A true Roadfood find. Jane and Michael, you may want to stop by as well!