I actually did the math once. You descend approximately 640 feet in the prison, and emerge at the same elevation that you entered. 640 feet doesn't sound like a whole lot until you consider that that is the height of a 64 story skyscraper. This was calculated using maximum human falling velocity without sustaining life-threatening injury, as well as duration of falls in cutscenes. The elevator descends 24 floors. The opening stairwell from the historical society descends roughly 170 feet.
@Dalton Frantz: From what I've heard, Silent Hill has been unofficially discontinued. Akira was the producer for the latter half of the series, and has withdrawn from the franchise. Konami does not expect to publish any more Silent Hill titles. Also, nice "Judgment" picture for your avatar.
Fatal Frame was really good, but the story was not nearly as compelling as SH2. The horror aspects were similar, though.
@K-nu: I'm sorry you didn't like the game. Unfortunately, this is one of those titles where you begin to understand how all of the characters interact after you have done extensive analysis of the story. The surface level content of the characters and plotline seems redundant and empty, but I assure you that there is a good reason for that. Some people like that kind of storytelling, others don't.
I have to agree with Yahtzee that this game is a game which really demonstrates how video games are a unique and transcendental medium of telling a story. Verily this story could have been told no other way. That having been said, I have read hundreds of books, seen hundreds of movies, and played (probably) thousands of games, and Silent Hill 2 is my favorite narrative of all time in any medium. Thank you, Team Silent.