Definition- A private boys school (grades 4-9) for one that is special located in Massachusetts. The students who attend are usually also known to be awkward with girls. At the Fenn School they hold a firm belief that one should express themselves fully.
This term may be also applied to any school that is bad at sports, "special," and/or generally disliked.
Simplified- A school you rip on.
"Dude who's that idiot over there"
"Oh, he's from the Fenn School"