The Original Green: New York's Street Grid

Applebaum explains how the street grid takes advantage of the elements:

"The early 19th-century planners who created the grid knew how to make the most of these attributes. They laid out the grid so that the sun sets precisely in line with east-west streets several times a year. The short north-south blocks mean more streets lead to the rivers, allowing floodwaters to recede easily and drawing people to the waterfront. The plan guided raucous commerce along the route of an old canal and enticed future developers with the promise of sites on hills with enviable views north."

Later generations of city engineers and planners failed to capitalize on the effectiveness of these early plans, and actively fought against them, says Appelbaum.