Does New York looks like a Middle Ages city? I think we must consider two aspects if we assert something like this because at first sight we can say nothing farther than that notion. However, I want to hightlight the contrast between open spaces and dark streets, shadows and lights on the one hand, and the city like a big market on the other. To my eyes, people move and run between shadows and lights looking for their own grail.
But I've seen something pretty curious: in Manhattan, the sight get lost in the space. You can see the skyline almost in every avenue, the horizon in Times Square indeed. The design of a medieval city is like a labyrinth, it seems as if chance or God's will traced the map (sometimes it seems the same thing). Most part of Manhattan is exactly a grid, so your sight can get lost in space and then it feels like New York has not weight. In the Middle Ages nothing has real weight except the Church. But the building of the church itself, forced you to look up there. And then, the sight got lost at the end. You find the sky, the real city god traced . By the way, Wall Street does the same!
Ok, we must think what kind of god we can find up there.