If you're stuck in Litchfield: Aspen Garden is a family-type restaurant with decent chicken parm and greek salads. Just watch out for the owner's girlfriend. Di Franco's has the world's best Veal Francaise if you don't mind people throwing things at each other in the kitchen.
Italian: San Marino's in Waterbury. Excellent service, reservations recommended. Average plate price $18 - $25, Roman night provides full meal & dessert for about $16 or $17.
Mexican: Salsa in New Milford. Small portions and less than perfect waitstaff, but it's a clean, open-kitchen place with good fresh food. Average plate price $10 to $14.
Best Chinese: Main Moon on the New Milford green.
Best burger: Marbledale Pub in Marbledale. Around $8.50. I've tried burgers everywhere and this is still the best.
Best steak: any Chuck's, they're consistent. $15 to $25 depending on cut.
Best Philly Cheese Steak: Widow Brown's in Danbury, about $9.
Best fries: Marbledale Pub or Widow Brown's (same owner).
Best pizza: Doc's on Lake Waramaug (in New Preston, do takeout because they're always packed), $15 to $17 depending on size and toppings. Another good pizza and best calzones is Naples in Avon.
American food: Bailey's in Brookfield. Service was excellent and prices were about $18 to $30, but the food was out of this world.
Best for a special occasion? Probably one of the Carmen Anthony restaurants. Consistently excellent food, excellent service, and a very clubby atmosphere.
Hope this'll help if anybody's looking...