Union Sq South, Greenwich Village

Union Square is one of those necessary but annoying places that every New Yorker and tourist has to deal with multiple times. The south part of Union Square is particularly crowded -- more so than any other part of the area. The subway entrance is right here and it's one of the biggest stops in Manhattan. Nearly every train system in the city joins up at Union Square so this area is a perpetual zoo. Add that to the fact that there's a market nearly every day of the year right here, and good luck being in a hurry and having to navigate through Union Square south.
There's nowhere to sit in the entirety of the square and Union Square South is no different. I have never once found an empty bench in the entire time I've lived in New York. And, the people that hang out on the benches here freak me out a little so I guess that's probably a good thing. Union Square South is where all of the punk kids hang out. It's not unsafe but let's just say it reeks of patchouli and there are a lot of skateboards zinging around. The area gets particularly crazy around the holidays because more booths go up on the south side. So, I try to steer clear of it.
Union Square isn't a real street, per se. You can't live on it and you can't drive on it. There are just about a million people on it every single day. It's this sort of vortex of people trying to get to other places even if that other place is just the north side of the Square.