That depends. The whole school system down here is pretty whacky. I swear the school board needs to put the pipe down.
I don't really know what to tell you. I went to Preptown (Leonardtown) and hated it, but then again I don't like the "shiney, happy people", that just act that way. Leonardtown, may look like its better, probably less violent than Great Mills, but the just many, if not more drugs. I've got more friends that graduated from Great Mills than Leonardtown, and since we didn't graduate all that long ago (I graduated 2001), we still tend to talk about high school a lot.
BTW, Leonardtown is on its second or third principal since I graduated, not sure about Great Mills or Chopticon.
As far Chopticon, if you don't mind sending your kid to a school that up until recently had its own barn, and had/has some students that think tractors are viable school transportation, that's on you.