Madison Ave Between 72nd St and 75th St

While certainly not part of Museum Mile (which is on 5th Avenue, 10 blocks north of here) the inclusion of the Whitney Museum of American Art makes it easy enough to consider these blocks part of the greater "Museum District". Lined with ornate buildings ranging from churches to retail stores, the block is masked in the beige wash of limestone.

Madison Avenue, especially on the Upper East Side, wouldn't be itself without a slew of high-end stores (and a shuttered Sharper Image) to entice walkers. All of this makes the unique Whitney Museum building all the more interesting. Finding the strange, avant-garde museum amongst the classic architecture is a bit like finding a spoiled hipster kid in Spanish Harlem: It's an interesting juxtaposition to observe, but you're not so sure it's the best place for him to be.

80th St Between 2nd Ave and 1st Ave

Staunchly residential and fittingly quiet, this part of 80th Street is a stereotypical Upper East Side block. With only a handful of neighborhood amenities surrounding the apartments, there isn't much to lure you down this way.

The western end of the street is more humble and quiet while the eastern end is home to more large apartment high-rises and condos. Seeing as this is further from the Subway, I was a bit perplexed by this. Usually the closer to the transportation you are, the better the housing. Oh well, shows what I know.

69th St Between 5th Ave and Madison Ave

Ah, the land of Service Entrances. On a block littered with townhouses and apartments (and one hot dog vendor), it's hard to imagine that any one would stand out.  However, about halfway down the street sitting quietly at #8 a swooping stoop curls up toward the current home of the Columbus Citizens Foundation. After buying the building from Sweden (yes, the entire country...they were using it was their NY Consulate) in the late 1960's the CCF began using it as their main headquarters and will often open it up for "cultural and social events". Ambiguous as those events may be, the few pictures I could find show that this building is no joke – especially its lavishly-decorated Oak Room.

Unfortunately, the inevitable result of this street is that you'll eventually end up on the criminally-boring and crowded Madison Avenue. I've gone on the record several times before that Madison Avenue is my least favorite street in Manhattan. I continue to stand by this. 

76th St Between Madison Ave and Park Ave

Fully entrenched in the Upper East Side (side question: should neighborhood names be capitalized? I'm getting mixed reactions), this block is only a few steps from the Whitney Museum, and as-such feels sufficiently high-class. There was a good deal of construction and renovation on this block – I guess the buildings weren't fancy enough.

You'll find three types of people on this street: People who live here, people looking for the Whitney and invisible people (seriously, it's like a ghost town).  Once you reach Park Avenue, things open up a bit and  the Lenox Hill Hospital is dominant on the north east corner - with half being brick and the other half being....some sort of turquoise thing.

5th Ave Between 66th St and 68th St

Many of the blocks along 5th Avenue that run the stretch of Central Park can blur together. Fancy buildings to the east, trees and a never-ending stone wall to the west. What does change, however, are the occasional landmarks such as memorial statues. On this particular section the 107th Infantry Memorial is one of the few defining elements.  Built in 1927, the statue is dedicated to the memory of 1078th Infantry Regiment, which was mostly comprised of men from the area.

By this part of the park, the highrise buildings in midtown begin to be obscured by the trees. The park itself is an ever-changing landscape which makes it the most interesting thing on the block – let's face it, the mostly generic line of buildings along 5th avenue rarely overpower the beauty of the park.

Madison Ave Between 68th St and 66th St

A street to rival 5th Avenue in terms of upscale shopping opportunities, the northern part of Madison Avenue is rife with boutiques. If you're not here to window shop, you'll feel a bit out of place. The glacial pace adopted by the pedestrians here can be quite a hang up for anyone trying to move it along.

Like the rest of Madison Avenue, these are more buses here than you can shake a stick at. I've been known to refer to the avenue as a glorified express lane - and that remains partially true. At least there's more to offer up here than down south in the desolate 30's.