5th Ave Between 40th St and 38th St

   

Walking south away from the New York Public Library, the wide-open avenue offers a clear view both uptown and downtown. Sitting between Grand Central Terminal and the Port Authority Bus Terminal these intersections are often busy with commuters at the beginning and end of each day. Walking between midtown and the bus terminal is often easier and quicker than taking either the Times Square Shuttle or the 7 train – especially since neither go all the way to the port authority without an extra block or two of underground walking (which in the summer is hardly worth it).

Lord & Taylor's flagship store begins the drop-off in major retail that's the hallmark of 5th Avenue north of 42nd Street. I find the Sleepy's "On Fifth" store to be a rather funny contrast to the Lord & Taylor signature. It's almost like the mattress chain store is trying to borrow a bit of the fashion department store's cache simply by using gold script.

Park Ave Between 37th St and 35th St

Park Avenue seems to have an uncanny ability to become a sweltering strip of molten asphalt in the middle of Summer. The double-wide street allows for more sunlight to peek through the buildings, and even though a great number of trees do their best to make up for it, you can still find yourself slowly melting into the relentless traffic.

The alternate side effect of this openness is the fleeting views you can get of many buildings and landmarks. Sure, some will enjoy the long stretch of (unworkable) parkland in the middle of the road, but I get more joy out of momentarily seeing the Chanin, or Empire State Buildings. It's a little bit of a surprise on a street where the expected view is generally just the MetLife building.

37th St Between 5th Ave and Madison Ave

    

A barren wasteland of construction and midtown offices, this block is only steps away from such tourist heavyweights as the Empire State Building and Lord & Taylor. Open up the radius a bit more and you're just a few more blocks from the Public Library and Grand Central. The result is a congested and generally unpleasant stretch of asphalt and concrete. There's a good representation of local shops on this block which could be considered a plus, but very few were welcoming or any more pleasant than a God-forsaken Chase Bank or Duane Reade would be.

This biggest benefit this block brings to the table is its architecture. The old buildings, some in better condition than others, each have their own charm, even if it is the charm of deterioration. Off in the distance you can see some more modern examples forcing their way into the skyline. I have no absolute problem with modern buildings – I'm probably more open-minded than most –  but the stark comparison between the craftsmanship of the old and the new is quite telling.

Lexington Ave Between 35th St and 37th St

   

Resting near what could be considered the southernmost boundary midtown, this part of Lexington Avenue seems lacking. Only a few storefronts brighten-up the otherwise dreary sidewalk. Some long-standing construction sheds, a few office buildings and schools make up the other features.

It would be hard to pinpoint a single defining characteristic that these blocks have. No architecture, no retail, no building-type nor any person seems to dominate any of the others here; leaving the street to wallow in mediocrity.

40th St Between Park Ave and Madison Ave

   

Branching off a busy intersection of Park Avenue which includes the transition from the Park Avenue Tunnel to the Park Avenue Viaduct, this stretch of 40th Street is unassuming and unwelcoming. While there's a certain polish tourists come to expect from the 42nd Street / Grand Central area, it's interesting to see how much the side streets deviate from that image – and it's not surprising either, since hardly any tourists venture away from Park, Lex or 42nd. These neighboring throughways are mostly home to weekday lunch spots, business services and other local joints.

The massive building on the north western side of the street, 285 Madison, has a tremendous collection of miniature sculptures surrounding each of its windows and entrances. The ones closer to the ground have been mostly worn away over the years, but gazing upward, you can see incredible detail in the ones that have been protected by their fortuitous perch. Surrounding the rest of the intersection are a bevy of midtown lunch options. The newest member of this neighborhood, 4Foods has an interesting "modern" approach in-which they leverage social media, technology and their website to allow patrons to create and promote their own custom burgers. A series of seats with iPads near the front entrance should give you some idea of how tech-happy this place is.

53rd St Between 1st Ave and York Ave

    

A major block if only because it marks the end of Sutton Place (York Avenue) on the east side, this segment of 53rd Street also acts as an exit ramp for the south bound FDR Drive. The street is mostly home to some pricier apartments and condominiums. Other than that, only a florist and an antique shop call this stretch home.

The primary beneficiaries of the FDR's exit here are perhaps the three competing parking garages. The one on the north side of the street has an ever-present attendant waving people into the bowels of his parking empire every morning. The other two seem a bit more laid back about their operation, content to let the remaining automobiles choose between them. Because God-forbid a person make it all the way to 1st Avenue without paying $45.00 to park first.