Massachusetts
Boston
Legal Seafood may be a chain and it may not be the best seafood in the world, but I have never had a bad meal at a stand alone Legal outlet. The Logan airport location just delivered the first bad meal I'd ever had at Legal so I can no longer claim "never" wholly, but well qualified I still recommend it.
Abe & Louie's is one of those "old boy" type places that you don't think exist any more. If you're a regular they know you and your palate extremely well. They know the table you prefer and the cocktail that you'll want waiting. If not, you may well want to become a regular.
East Side Bar & Grille in Cambridge is my go to place for a good cocktail or a well poured beer and a low key atmosphere. Get a baked quahog and a salad with your Harpoon IPA and you're golden.
Western MA
Eastside is the place I jones for when I'm away. They have a good caesar salad and serve it with anchovy (as the food gods intended!). They no longer plate my favorite fish dish, but always have a nice selection of fresh seafood. Try the sweet potato chips with artichoke and crab dip. I have no idea why they don't put it on the regular menu because it's been on the specials list every time I've been there over the last three years.
Carmelina's in Hadley is a new fav for me. Was just there this month. It's easy to say that it's charming, but what you wouldn't realize from the exterior is that you'll get some of the best service inside this unassuming space. Paired with great ambiance and live music and you start to understand why it's always packed.
Esselon, also in Hadley, is one og my favorite places to grab breakfast or brunch. They have a lovely gardenside patio to enjoy while injesting amazing carb laden breakfast goodness. If I liked coffee I have no doubt I'd love theirs. It smells great!
Green Street Cafe, in the shadow of Smith college, serves a small but very fresh menu in a converted storefront space that can feel a little odd, but none-the-less quite welcoming. The service tends to be a little on the flighty side, but the food more or less makes up for it.
Cape Cod
http://www.yelp.com/biz/edwige-provincetown in Provincetown is ideal for a romantic dinner with cocktails, but be forewarned, it's small, bustling and can be quite hot when the weather heats up. They win points for great cocktail concoctions.