Yeah I know the history. But believe it or not those grids are easy. You can make all the grids of Brooklyn out of like 6 Jigsaw pieces. There's a directly south portion that leads to the lettered Ave's all the way to CI, a "Manhattan South" portion that hugs the coast, a "Carnarsie South" portion that hugs the coast East of Coney Island, Bushwick Cheese slice, and Williamsburg offset from there. Easy Pz. The grids of Queens north of the subway are also pretty easy to split into a manageable number of jigsaw pieces, namely Astoria (follows Manhattan convention), everywhere East of LGA up to and including Flushing (true north). Its the border zone between BK and Queens that just refuses to admit a nice, simple, summary pattern. Pretty much everywhere due East of Newton Creek and/or along the lower Montauk is a mess.

Most likely this is because that particular region either had unfortunate geographical components or because the settlements there were much smaller and therefore not nicely aligned. You see a very similar thing if you look at the map of Amsterdam. The bigger developments are all nice and orderly and result in clearly recognizable patterns, but whenever the 'new' butted into the old it becomes messy.

Quite a few small towns found themselves suddenly as components of Amsterdam after being engulfed. New York in a way is relatively orderly because all of that happened in a short time.

It's fascinating stuff. Good luck with your search, I'm curious if you ever will find out what caused it.

I've looked at some really old maps. Like this one from 1853 [1]. So for starters, the Long Island Railroad is apparently eternal as its nearly impossible to find a map which pre-dates it, the modern subway lines bare remarkable resemblance to the former "plank roads", and above all the regions that I'm finding most difficult to reconcile are actually younger not older than the other grids that have been stitched together.

This helpful tool [2] highlights what I mean. Zoom out and look around, its mostly consistent large jigsaw pieces. There's just this one turbulent maelstrom in the middle that ruins the idea of several grids glued.

1. https://www.loc.gov/resource/g3804n.la002117/?r=0.197,0.358,... 2. http://www.datapointed.net/visualizations/maps/enhanced-stre...

Could it have been some large company that held the land and put their own buildings on it? There are some regions around here that are as large as the cities they border but are private land, Hoogovens (now Tata Steel) in IJmuiden is one of those and near Rotterdam there is 'Pernis'. Inside those it is a huge jumble. Other options: swamp land, native American settlements, army installations. Bushwick loosely translated is 'Boswijk' aka forest borough, so the area may have been heavily forested. The roads there may then have been logging roads rather than roads for regular traffic.

>Could it have been some large company that held the land and put their own buildings on it?

Coincidentally that describes an area a bit north of where I'm focusing called "Rego park". Where does the name Rego come from? Was it what the Native Americans called it before the settlers arrived? Was it the name of some important person in history? Nope. None of those. The company that developed the area was called "Real Good Realty". Rego is a contraction of REal GOod. Yep, its that stupid. But Rego Park is still grid conforming.

There's a bunch of strangely curving streets a bit East of Rego Park in a crescent shape starting at 63rd St. Those are bending around the (now abandon and overgrown) tracks of the LIRR Far Rockaway branch. That line continues straight South exactly tangent to the curve. There's a few other places on the map where long gone rail lines influenced streets, but those mostly form minor exceptions to grid rules rather than full on dissolution.

You're right Bushwick was absolutely Forrest from what I've read. But Bushwick itself is actually pretty grid conforming. Its approximately rectangular and slightly rotated relative to Bedstuy on its left side. The difficult parts start just above Bushwick. Namely around Ridgewood, Glendale, Maspeth and Middle village.

Queens is unusual in the sense of having developed incredibly recently. Like literally farm land as recently as the 50s in some parts. Logically it should be the most conforming to the overall street plans, yet it isn't. Yeah there's natural borders like those cemeteries, but if it had streets running along the edges of the cemeteries the result would be a square layout leading exactly to a grid! Its almost like someone went out of their way to avoid making sense!

BTW since you're interested there's quite a few place names in NYC where the influence of the Dutch settlers can be seen. New Utrecht Ave, Dyker Heights, Stupyen Duvil, Yonkers, Van Nest...probably more but those are the ones I can think of off hand. There's also the flag of the city [1] which still has the blue-white-orange banner of the Dutch crown (albeit vertical rather than horizontal). I've been told in recent times that particular tri-color pattern has an unfortunate association with far right political movements. Is it true?

1. https://www.crwflags.com/fotw/images/u/us-nyc15-l.gif

> New Utrecht Ave, Dyker Heights, Stupyen Duvil, Yonkers, Van Ness, Van Wyck...

I'm aware of them, just figured the point had been made. There are indeed quite a lot more of them if you know how to look for them. The degree to which they have been bastardized sometimes makes it harder to spot them.

> There's also the flag of the city [1] which still has the blue-white-orange banner of the Dutch crown (albeit vertical rather than horizontal). I've been told in recent times that particular tri-color pattern has an unfortunate association with far right political movements.

The 'Prinsenvlag' (the non rotated version) is indeed associated with the NSB, the Dutch Nationalist Socialist Movement which during World War II made nice with the Nazis and whose name is pretty much synonymous with 'traitor'. In more recent times it has been associated with the PVV another right wing party with nationalist tendencies.

If you zoom it it gets less neat. In the Williamsburg/Greenpoint area you can see 5 different grids. All of them historically from different settlements.

Williamsburg/Greenpoint is several pizza slices of grid arranged in a semicircle around a common corner. Sure its 5 minor grids but its still very much a simple pattern to summarize

* * *

The major impetus for unification was the promise to build the subway. Manhattan had the money but needed the land, Brooklyn and Queens had land but not the wealth.

Once upon a time Flushing was hyper religious Quakers. When the NY & Flushing RR was built (today the Port Washington branch of LIRR), one of the anecdotes in its history was the moral outcry when they tried to run a single train per day on Sunday. They appointed actual fun police to make sure no rowdy drunkards would dare come to their town hoping to have a good time. What do they think this is, Brooklyn? LIC was literally built by and for the railroads. Before the tunnels into Manhattan (1906 IIRC), you would get off the LIRR (or other competing services which were later bought out) and switch to a ferry to cross the East river at Hunters Point. LIC was always de facto colonization by Manhattanites.

> Once upon a time Flushing was hyper religious Quakers.

That's not surprising given that the town of Vlissingen that it is named after in NL is also in part of what is called the Dutch Bible Belt. Zeeland has a very strong religious tradition, even today. Likely those that came to America and named their town Flushing (likely phonetically much closer to Vlissingen in those days) were from there.