North Stamford to the Inn at Pound Ridge is a very easy backroads drive of about 25minutes each way, and the food is delicious there. They have valet parking most of the time, a good drinks menu, and the brunch has a crispy rice squares w salmon item that is interesting and tasty. It is a bit more upscale than most of what we have in Stamford (it is a Jean George).

Without leaving North Stamford, you might consider (newer in the last 2 years) The Farmhouse at The Crossroads. https://www.farmhouseatthecrossroads.com/

I have been three times now and found the food to be delicious. Their seafood supplier is really hooking them up (the shrimp cocktail was magnificent). They have a great drinks menu, and the interior has a nice fireplace ambiance on brisker nights. They have a big outdoor area that they are ready to trot out for outdoor brunch w drinks once it is a tad warmer. It is more like a 5min drive from anywhere in North Stamford, so a quick/easy one. But menu is large and upscale decor, and it feels splurgy when you are there.