5th Ave, Madison Square

The area around Madison Square Park is pretty cool. And, 5th is one of the better streets here because not only is there a park view, but the buildings are not too hard on the eyes either. There's a massive old building that takes up the entire block between 23rd and 24th that houses the International Toy Center (weird, I know). It used to be a bank but the site has held many things including the Madison Cottage (a suburban lounge) and the Fifth Avenue Hotel which was one of the grandest in its time (1858-1908). There's a gorgeous clock right on the corner that is a relic of the time before wrist watches. I feel like wrist watches are going to be a relic in the not so distant future which will make the clock even more interesting. This side of the park has a William Seward statue ( I think statues of humans are equal parts scary and beautiful so I like this guy) and a WWI Memorial.
The next block up houses the park on the east and a green square on the west. It's really unusual for a city block to have green on both sides so this stretch is quite the commodity. There are memorials on both sides of Generals that I've never heard of but the real draw is just the green. You forget how much you miss a little grass until you live in a place where there barely is any grass.
There are some beautiful buildings on the next block leading up to 27th that mostly have businesses. The corner at 27th used to house Delmonico's which was the most fashionable restaurant in New York history. I'm sad I missed out on it because it seems to be mentioned in just about every historical city book. The building next door has a great current restaurant called Dewey's. Flatiron isn't known for its restaurant scene but they're really starting to make headway and this is a staple. It doesn't hurt that its building is incredibly dramatic looking. It even has bay windows which happen almost never around these parts.
The park is one of my favorites in the city though it's too small to feel like you're removed from all of the hustle bustle. Still, it has a great energy and the people watching on a nice day is hard to beat here.