The Stockyard in Brighton, Mass. Used to go her with my folks when I was a little girl, and it was the place we (Matt & I) went for a great steak dinner even during the lean Harvard years. We still stop in when we are in the neighborhood, This place is a gem.
Michael Symon's B Spot (Woodmere - in Eton Collection). Best burger place EVER. The Lola (fried egg) and Shroomage (well, mushrooms) are among my favorites. And the coffee BBQ sauce goes with EVERYTHING.
Wine Cellars of Annapolis (MD) - LOVE this place - every Saturday free wine tastings; and if you like what you see/drink - you can buy it - and if you get hungry there is a wine/food bar right next door or you can try Tastings Gourmet (also next door)