Starting quaintly-enough with a handful of older buildings and restaurants, this stretch of 88th Street quickly evolves into a series of high-rises apartments which seem to dominate over the more timid structures. In the middle of the block #230 E88th sits uncomfortably between far more attractive apartments. Near 3rd Avenue, the squat Valley National Bank feels incredibly out-of-place and tacky. Even a luxury condo would fit better on this lot – such as the unfortunate one across the street.

For all its flaws, the rest of the block is well-served by the turn of the century buildings which each have their own individual character and charm. It's a shame that just three buildings can so drastically shape one's opinion of a neighborhood.

Just a few streets south of its terminus, York Avenue still maintains the residential neighborhood feeling that dominates the majority of its 39 block existence. Both the street and the sidewalk here are very wide, wider than they'd even need to be. The stores feel a bit anemic for a stretch this large, but I guess there's a finite number of people living to the east of here, so it's not entirely necessary to be inundated with bars and dry cleaners. Save for a single Chase bank, I can't recall one chain store along the route. Even pharmaceutical needs are provided by a small shop rather than a Duane Reade. 

Something that has always caught my eye here is the number of dogs left tied up on the sidewalk while their owners go inside stores to shop. Recently EV Grieve mentioned a reader which was fed-up with this practice and has vowed to confront every owner they see doing this. I can't imagine I would ever go that far, but it can be a bit troubling. I'm not so concerned for their physical well-being–unless it's unreasonably hot, I don't think they're in any danger–as I am for their psychological well-being. I've never owned a dog, but they seem to endure some legitimate distress when separated from their owner. I find myself just wanting to give them a pat on the head to let the know it'll be alright–though I never do, both because I know it won't help, and God forbid the owner sees me touching their dog without permission. No, the neurotic in me tells me to resist the urge.

It seems that the tiniest of blocks are always the ones to be made narrower by massive trees in the middle of the sidewalk, trash bins behind obstructive fences and gargantuan stoops jutting out from their buildings. You rarely see these sorts of obstructions on the larger blocks, the ones that wouldn't be impacted by them. Following this backwards formula to a tee, this block feels like an obstacle course. If, while on this street, you encounter anyone walking the other way one of you will inevitably have to wait to allow the other person pass. There's a certain charm to all this maneuvering. It's a feeling of community by proximity–even if it's entirely artificial and only lasts for a second.

The trees which block the sidewalk also do a tremendous job of blocking the sunlight. With the specks of light fighting their way through to reach the ground, it's a marvel that this street isn't depressing. Quite the opposite, though. The residential atmosphere comes off as welcoming and laid back. It's not fancy. It's not full of buildings reaching for the sky. It's simply an unambitious and unpretentious block which is completely enjoyable to walk down. Granted, that's all you'll be able to do is walk…I can't recall a single business, save for a dry cleaner, that wasn't technically on First or Second Avenue. But be that as it may, with bustling industry bookending the street and chain hotels visible in the distance, it's great to have a block on which things slow down–if only for the moment that you're forced to let someone else pass by a tree.

Walking along Second Avenue you get the sense that you're experiencing history. For an entire generation Manhattan hasn't seen a new Subway line constructed. With a few exceptions the streets of the city have remained un-scarred by the destructive work required to build the world's largest mass transit system. But now, after nearly 80 years of planning, we finally get to see what it's like to be horribly inconvenienced by a massive public works project, the likes of which haven't been seen since our grandparents.

Granted, in the early 20th Century the construction methods were far less kind to the street. Using cut-and-cover to essentially turn New York into a series of ditches the original IRT system was built in just a few years (the brute force method I guess you could call it). Now modern techniques allow TBM's to work silently 10 stories below the surface. There will be a bit of cut-and-cover used during the construction, but nothing on the scale of the original. And unfortunately it now seems to take decades just to get the simplest things done. However unlike the early 1900's, the worst we have to deal with is narrower sidewalks and re-routed traffic. But it's still fun to look down into the holes dug into the street and think that such construction hasn't been seen here in quite some time. 

The vast open avenues that run north of the Queensboro Bridge enjoy an uninterrupted run that few other stretches experience anywhere else in the city. For example, First, Second and Third Avenues are able exist without without so much as a park or a detour getting in the way for over 120 blocks, before they all terminate around Houston Street. As a result, with the exception of the bridge, you can see clear down the streets here.

Thanks to the lack of any Subway connections and abysmal bus service the Upper East Side has remained a mostly-residential part of town for the duration of its existence. The combination of these large, midtown-like streets and the family-friendly neighborhood vibe create for an interesting dichotomy. You'd normally expect to see large office buildings lining these blocks, but instead you have drug stores, cafes and bodegas. The chains have certainly made themselves at home with Chase and Duane Reade making their presence quite well-known, but classics like Goldberger's Pharmacy seem to have held their ground.

A generic high-end apartment building known as The Laurel went up in the past year right next to a beautiful church. My first reaction was that it felt wrong and unfortunate. But really, isn't this what New York is about? The old and the new living together, regardless of style or intent? It may not be widely appreciated, but I think there's a lot to be said for the fact that the church is still here.

How many times have you found yourself watching a movie or TV show and wondered where the person with the amazing apartment that's magically close to everything is living? They're living on this street. I'm certainly no location scout, but this block has so many perfect vignettes and scenes, I wouldn't be surprised if it's already been re-created brick-by-brick on some backlot out in California.

While the block features a lot of variety in terms of building types and styles, they're far enough away from each other so that you'll always feel immersed in one era. For example, several mid-century apartments line one side for as far as you can see, meanwhile directly across the street an incredible-looking Mechanic's garage sits alone next to a church. Frame correctly by a director this could easily look like 4-5 different parts of town.

The street itself is dark and covered from end-to-end with trees. The narrow street can cause some headaches with drivers, especially when there's a moving truck trying to do its thing for a few hours.