I lived in New Canaan for 4 years.
It really sucks because if you don't have money or you're really ugly you are pretty much worthless. Sports are like oxygen to these people- well only sports that bring home championship titles, the other ones are treated like shit. Everyone has pretty much grown up together and everyone knows everyone. If you're really unfortunate looking, you can buy your friendship with cars, clothes, booze, ect. And drugs are pretty big. Not as big as Ridgefield though. Nearly everyone drinks, many people smoke weed, and some people do coke or oxycontin or whatever. The police are all itching to search teenagers because they are just as bored. Mainly people either hate New Canaan or like it. I'm indifferent because the people are mostly very nice, just not to those that are unattractive, lower middle class, or shy. Overall its a great family oriented place. Once you're older though, there's absolutely nothing to do except drink yourself into oblivion.
New canaan is a nice place to live if you are attractive and wealthy.