A couple of places to consider:
For dinner or lunch - Horsefeathers (right across from the train depot) has a good variety on their menu, including burgers, pasta, etc. Love the chicken quesadilla!
For breakfast/brunch - Sunday breakfast buffet at Red Fox in Jackson. For $7.95/per person, it can't be beat. Awesome selection, and the best omelets!
Shalimar- great Indian food
Moat Mountain Brewery- very tasty, always consistent.
For Breakfast- The Blueberry Muffin.
Delaneys is good pub food and has entertainment.
For a romantic night out I would highly recommend the Stonehurst Manner.
For a tasty lunch, Chef's market has great prepared foods and wonderful sandwiches. I also recommend going to Echo lake for a swim, beautiful views of Cathedral ledge.