50 State Quarters Rated: 2000

Massachusetts
Okay, maybe I'm partial because this quarter features my home state and depicts a statute located in my home town. But in my opinion, this quarter is exactly what a state quarter should be: outline of the state, important icon of the state, state nickname, and that's it. I still think that "The Bay State" isn't a particularly descriptive nickname for the state, but we have to work with what we're given.
Rating: 25¢

Maryland
The structure in the center is supposed to be the dome of the Maryland state capitol. It's framed by two random branches and an off-center nickname. Blah. My feeling is that you should be able to look at the picture and immediately know what state it belongs to. Oak trees could be anywhere, and while I'd have a fighting chance of recognizing the Maryland state capitol if you showed me the whole thing, I can't do it by the dome alone.
Rating: 5¢

South Carolina
This quarter borders on having too much going on, but doesn't quite cross that line. The state outline, the iconic palmetto tree, and the nickname are perfect. I don't think the star for the capital is necessary, and while I don't know what the bird and the flowers are supposed to be, at least they look pretty.
Rating: 20¢

New Hampshire
It features the Old Man of the Mountain, may he rest in peace. That's about it. Yeah, you have the state motto also, because New Hampshire is proud of its "Live Free Or Die" heritage. The nine stars represent that New Hampshire was the ninth state that ratified the Constitution. While the stars do a nice job of completing the circle, their symbolism doesn't strike me as particularly important. All in all, though, it's a bold yet simple presentation of what is clearly the state's most preeminent icon.
Rating: 20¢

Virginia
The settlement of Jamestown -- the first colonization of the Americas by the English -- is undoubtedly an important event to commemorate. But, technically speaking, the quarter does not commemorate the settlement. Instead in commemorates the quadricentennial of the settlement, which was schedule to take place seven years after the quarter was issued. How can you commemorate something that hasn't happened yet? Otherwise, it's a pretty nice picture that would benefit even more from the addition of something else (not sure what, but at least something).
Rating: 10¢