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The Commissioner's Plan of 1811
A little over two hundred years ago, the original design plan for Manhattan's streets was finalized, forever defining the grid pattern that is so closely associated with New York all these years later. Many believe it to be "the single most important document in New York City's development" and it is easy to see why. New York had, till that point, been developed in an organic way, the streets were more likely to follow well-trod cow paths than they were to have any semblance of external order. However, the city's population was booming and the financial and commercial possibilities of expanding the city in an orderly, deliberate way were seductive to many of the people who were running the city. Much like the present day bike share, the street grid plan was sold to the population as a public health measure, with the City Council claiming "laying out Streets... in such a manner as to unite regularity and order with the public convenience and benefit and in particular to promote the health of the City ... [by allowing] a free and abundant circulation of air" to prevent the spread of disease.
But, much like the bike share, there were protests by people who can best be classified as "not in my backyard"ers, people like Clement Clarke Moore (famously the author of "Twas the Night Before Christmas"), who protested the grid's affront to Manhattan's natural beauty and, of course, to his own estate, which would be divided up in the plan. Moore said at the time, "The great principle which governs these plans is, to reduce the surface of the earth as nearly as possible to dead level. ... The natural inequities of the ground are destroyed. and the existing water courses disregarded. ... These are men who would have cut down the seven hills of Rome." Moore wasn't the only famous person who hated the plan. Henry James said the grid was nothing less than a "primal topographic curse," and Alexis de Toqueville disparaged the plan for its "relentless monotony."
However, despite these naysayers, the grid persisted and it's hard to imagine the city laid out in any other fashion. I can't even bear to think of how confusing it would be for the millions of tourists—who can't even grasp the simple elegance of the grid system—had to navigate a whole borough laid out like the West Village. Plus, without the grid system, there would never be Manhattanhenge. And Manhattanhenge is amazing. All in all, I think this was a win for the city.