No - don't do it! Despite its popularity as a tourist destination and its quantity of restaurants, Litchfield is woefully bereft of decent food. Having tried West Main restaurant, which was okay, we passed it up this time as the cheapest dish is a $14. burger.
Aspen has a pretty outdoor seating area, so it was full. The inside is a typical diner with no character. The menu has Greek and Italian dishes plus the usual burgers, etc. I cannot tell you how lousy every single dish was. The Greek salad was wilted iceberg lettuce, 3 olives and one tomato chunch cut in two. There were a few bites of feta cheese. When I asked where the feta was I was told that it really wasn't part of the salad. No anchovies, peppers, nothing. Rolls were out of a bag. Gyro (only beef, no lamb) had defrosted patties and an utterly bland tsazaki sauce. Need I go on? Oh - the kitchen was excrutiatingly slow and the waitresses got snippy when we asked for our food already.