50 State Quarters Rated: 2001

New York
What do you associate with New York any more than the Statute of Liberty? I didn't think so. Yeah, there's the rest of the state also, which is appropriately recognized through use of the state outline. I've never heard the expression "Gateway to Freedom" used in conjunction with New York, and the stars are once again unnecessary, but by following the same aesthetic structure of the Massachusetts quarter, this one works.
Rating: 20¢

North Carolina
The Wright Brothers's flight is a perfectly legitimate subject for this quarter. The extremely horizontal orientation of the picture bothers me for reasons that I can't quite articulate. I also wished it would say "First In Flight," like the license plates do. But it's a pretty good depiction of an important event, so I can't make any major objections.
Rating: 15¢

Rhode Island
This picture is gorgeous. While Rhode Island tries to make itself out to be this nautical state, I spent five years there before and after college and saw the actual ocean maybe half a dozen times. Whether it's accurate or aspirational, the quarter captures this sailing scene perfectly. Very few state quarters are effective tourism advertisements. This one is.
Rating: 25¢

Vermont
I'd say that a hammer and sickle would be the most representative thing that Vermont could put on their quarters, but the idyllic New England scene of tapping maple trees for syrup works as well. The quarter even contains a shout-out to the Green Mountains in the background. I'm not crazy about the motto, but I can deal with it.
Rating: 20¢

Kentucky
I think that the dual themes of horse racing and rich white Southern gentlemen would be better captured by a scene of Churchill Downs, but this image will do. It's large and commanding without being overly busy. My only suggested change would be to replace "My Old Kentucky Home" (it's the title of a song, not a slogan) with "The Bluegrass State."
Rating: 20¢