Madison Ave, Madison Square

This stretch of Madison Avenue is one of the only parts of the street that takes even a tiny break from its almost entirely commercial run. Maybe that's why I like Madison Square Park: it's a nice breath of fresh air in a crazy part of town. Granted, that kind of crazy takes away from the park sort of vibe, but the park is still pretty cool. And, its being surrounded by behemoth buildings is a very New York picture to me.
Madison at 26th has the Merchandise Mart on the northeast corner. It's a really ugly building with china and silver showrooms inside, but luckily, buildings like this aren't abundant in this part of town. There used to be a mansion on this site and it's such a shame that this is what replaced it. The south side of the block houses a courthouse -- really weird place for a courthouse, I know. But, I guess it was here first so what can anyone do? Nothing like a burger and a petty crime, right?
The Credit Suisse building is at 25th. It's a massive business building with nothing noteworthy in it aside from Danny Meyer's two big time restaurants 11 Madison Park and Tabla. 11 Madison won the James Beard award last year but I think it's too pretentious. I prefer Tabla of the two though it's not nearly as exalted by foodies. They are both insanely expensive, though, so be warned. Just down at 24th, in the park, is the way cheaper Danny Meyer shoot, the Shake Shack. It's a perpetually crowded but delicious hamburger stand that every New Yorker has to try at least once. Finding a seat on a nice day, though, is like finding Xanadu. That's how popular this place is.
As far as the park goes, the Madison Oak tree is on the Madison Avenue side. This tree was taken from Madison's actual estate and planted here to commemorate him. And, there are a lot of lovely sitting areas. This park has a lot of wonderful history to it though it doesn't look particularly historical anymore. Herman Melville used to walk here every day and it is the site of many O. Henry stories. It's a pretty cool park and apparently used to be really cool.

Not to be confused with entertainment behemoth Madison Square Garden, this quiet enclave of greenery at Madison and 23rd Street is a bit of a curious apparition: a park and sitting area in the midst of the bustling border between mid- and downtown. The area is pleasant enough for a business center - the Flatiron building is a welcome sight (and the coffee shop next door is one of a diminishing number of "proper" city coffee shops), although the downtown stretch of the square is dotted with decidedly unappetizing fast food franchises. It's not a place to live, though; much of the entertainment and dining options are limited to takeaway of varying quality (the Morton Williams near Union Square offers perhaps the most wholesome fare, on a budget less than that of nearby Whole Foods) and a few interesting looking business-lunch joints. That said, as hard as real estates try to sell the area as NoMad (North of Madison Avenue), it's not so much a neighborhood as a business nexus. Still, if you're going to have to spend most of your days in an office, you could do worse than pass by the scenic Art Deco buildings around this area - and NoMad, name aside, is among the more pleasant places you could work. You're near the Union Square and Gramercy Area, for starters!