If you're in the mood for kitschy, try Rosy Tomorrows in Danbury Connecticut. Part of it is an old railroad caboose attached to an old house. The place is full of remnants of the old Danbury Fair including the fortune teller, the funny mirrors, and other fun stuff. A train even runs above the bar, you just insert some coins and the money goes to charity. Model airplanes and rowing shells hang from the ceiling.
The food is good, my favorite being the Buckshot Burger shown above. It has horseradish dressing, onion straws and cheese on a nice toasted kaiser bun. With it you get a generous portion of sweet potato fries for $10.50. My second favorite is the blue cheese burger where the blue cheese is put in the middle of the burger. That one has bacon on it. I also like their French Onion soup and they make an interesting six-layer flower pot salad.
They have a good beer selection too, including a house ale which is pretty good. We've been there a few times and we took the grandchildren once. They loved all the stuff hanging on the walls and from the ceiling.
Overall, an interesting dining experience with good food at reasonable prices. Check out their website for more information.