Two pages and no one has mentioned Davis' Pub in Eastport? Best pub food in Annapolis.
If you don't mind a bit of a walk, Lemongrass on West Street in Annapolis is quite good (Thai).
Osteria 177 on Main St in Annapolis is the best Italian in town.
Snapper's in Cambridge is pretty good. Zanhiser's Dry Dock in Solomons is good. Robert Morris Inn in Oxford is quite good. The Rusty Scupper Sunday brunch (Baltimore) is very nice.
I'd be remiss if I didn't mention Eastport Yacht Club (must be a member or guest) that has a very good kitchen.
Sam's is nice, but overpriced.
Cantler's is a pit, and Chick & Ruth's is a greasy spoon. Neither is worth a visit.