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One of the best restaurant in Gloucester is Duckworth in East Gloucester. Eating at the bar is a special treat for one or two, because the bartenders are always fun and entertaining. Everything at this restaurant is fantastic, but sticking with the specials has always produced a very memorable meal. Save room for dessert. The chef's wife makes them all from scratch, and they're very much worth the strain on the waistline.
A little less expensive than Duckworth, much larger, and also consistenly good is Franklin Cafe right in the middle of town on main street. It's a bit dark though - reading the menu is difficult for those over 40. The specials are always a good bet, and their signature pork dishes always impress. The upscale menu, however, is NOT child-friendly.
The White Rainbow is a decent bet as well.
Ocean View Inn and Resort has just hired a new chef from France for its Ocean's Edge Restaurant. They have come out with a new early bird specials menu called "The French Connection" that is expensive but sure to please the most discerning diner.
Captain Carlo's is downtown and located in the Harbor Loop opposite Main Street Plaza. It's got seafood items popular with tourists, outdoor waterfront dining, a nice bar, and very attentive service. Until recently, Whoopi Goldberg was a regular fixture at Captain Carlo's, helping out behind the bar and trying out new comedy routines on the crowd.