[CydeWeys]

We're fortunate enough here in NYC that it doesn't get down to Toronto-levels of cold very frequently, meaning that the construction of something similar to the PATH hasn't been necessary. I think the superblock layout would work pretty much unedited here. There might be a few super cold days in some winters that'll make you just want to hate life, but the subway is already the solution that most people use for that, and adding superblocks isn't going to make anyone's walk to the subway any longer -- it'll actually make it shorter, since there's fewer pedestrian crossings to stop for.

I like the other commenter's idea of above-ground enclosed passages with access to sunlight and windows. That sounds need. Vegas actually has something sort of similar on the Strip, but for different reasons. I think that, at least in NYC, something like this is orthogonal to the issue of superblocks; most people already aren't using cars to escape the warmth anyway, so if this kind of solution were necessary it would've already been made, with superblocks having little effect.