From worst to better...sort of
Sakura is mediocre Japanese food produced by people who speak superb Cantonese. Tasteless sushi is best eaten with a Thai sensibility (with lots of wasabi to liven the long dead fish) and every non-sushi dish has too much deadly death food-kill sauce which is more often than not Chinese black vinegar-based.
Taipan, at least in my experience, is Thai-ish food misinterpreted through a think fog of dense and stale Chinese flavors. Avoid the tasty sounding appetizers and order the more Chinese-ish main courses if you choose to eat there, as its a Chinese person that's preparing your food and not leaving the purview of his knowledge when you request such things.
Little Kitchen-radically erratic, though 20% of the time on the money, with a random home run thrown in for confusion. Chicken with crispy spinach is the best dish I have had there--even if the spinach is not cripy, the sauce with rice is so good that you won't care. 1 in 10 seafood dishes is brilliant, while the other 9 in 10 are shipwrecks. Its a lottery, but with so little good food in Westport, you kind of have to gamble.
Angelina's-greeza-some combination of greese oil and baked (deep fried?) dough called pizza.
Aqua-it could be good. The pizza and seafood are nice sometimes (nice IS the word I am looking for); and its actually a rather pleasant place to sit in the summer. Food has pretensions that belong in the suburbs though-often excessive ingrediented dishes that fall flat.
Oscars-impressed me 3 times, I kept hoping it would change, by rudely producing the worst bagel and cream cheese (the cream cheese was the culprit) that I have ever had. This is a Jewish deli? Reubens are actually OK, and some people, though not me, are hotdog fans.
Gold's-much better deli than Oscar's, though that's not saying much. Lunch sandwiches just short of first rate.
Bombay Bar and Grill-very saucy with not particularly fresh ingredients, but, hey, that's often what Indian food is. Its not good, but its not bad, and in the context of Westport, that means its damn good. The sheer variety of spices makes it kind of fun, though best not visited too regularly lest you exhaust the limited capacity of the place.
Westport also has a relatively new Indian rest across from the post office that I have tried once and seems to have NO business (not usually a good sign). It was OK, not enough trips to really comment on one take out lunch.
Onion Alley-Britishy styled American food anyone? OK burgers.
Tavern on Main-deceptively good. Looks like a boring pub on the outside and on the inside (trips through the English countryside have trained me to avoid Pubs), but someone in the kitchen actually has a sleepy talent that awakes in dishes at random moments. I had an excellent salmon dilly appetizer there, and staples like hamburgers are very good, though I have also had things that were bad. Go with many, something will be a lovely surprise.
I can't comment on the expensive restaurants in town as I have never eaten at Miramar or DaPietro, and tend to migrate to NYC on weekends for fare requiring expense, since there seems a higher probability of success for $100-200 a person.
Coffee 'An I also recommend. Jelly and all chocolate donuts good, glazed and chocolate glazed even better. Pictures of owner with various politicians on the wall and the regular clientele are perhaps the best. A dose of mild surrealness.
And leaving Westport Fairfield Ole Mole and Stamford branch somewhat erratically kicks ass. Still almost always better than almost all of Westport possibilities. Not had anything that was only OK, which is very good.
In Norwalk, Meson Galicia is by far the best food I have had in CT. Order lots of appetizers and be taken away on a most excellent culinary trip to Spain. Very well balanced and fresh and refreshing and interesting. It ain't cheap eats, but then again its cheaper than about 70% of similarly styled restaurants in Manhattan. No, no, of course its not Daniel, but its probably as close as you will get within 10 miles of Westport.