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Manhattan's street plan was drawn before the city reached it. The Commissioners' Plan of 1811 laid a rectangular grid from Houston Street to 155th across farmland, valleys and streams, straight over two existing villages, without much regard for topography or for who owned the ground. The city then grew north into a map that was already waiting for it. Broadway cuts diagonally through the whole thing because it was a road before the grid was an idea.
Not a building but the thing you are standing in. Twelve numbered avenues running north, cross streets running east and west, imposed in 1811 on land that was mostly farms. Hills were levelled and streams culverted to make it fit. The regularity that visitors find so navigable is the result of ignoring the terrain entirely.
The diagonal that ruins the grid, and the reason Times Square, Union Square and Madison Square exist: they are the leftover triangles where an old road cuts across new right angles. Broadway predates the 1811 plan and was not part of it. Every irregular public space in midtown is a scar from that collision.
Eight hundred and forty-three acres of entirely constructed landscape, laid out from 1858 by Olmsted and Vaux. Nothing here is natural except the bedrock outcrops. The park displaced Seneca Village, a settled community of largely African American landowners, which the city cleared by eminent domain and which was written out of the story for a century.
A 1913 station whose real achievement is underground: two levels of tracks buried so the land above could be sold and built on. Park Avenue runs over the train yards. The ceiling's constellations are painted backwards, which has been variously explained as an error and as a deliberate view from outside the celestial sphere.
Opened in 1883 after fourteen years, the first steel-wire suspension bridge. Its designer died of an injury sustained during surveying; his son took over and was disabled by decompression sickness from the caissons, after which his wife Emily ran the project on site for years. The bridge was substantially delivered by someone who was never formally its engineer.
A freight rail viaduct built in the 1930s to lift dangerous street-level trains above the West Side, abandoned in 1980, and reopened as a park from 2009. It was slated for demolition. It is now among the most visited sites in the city and has demonstrably driven up property values along its entire length.
A preserved apartment building on the Lower East Side, kept in the state successive immigrant families left it. It was sealed and unoccupied for decades after the landlord declined to fund required upgrades, which is precisely why the interiors survived. Neglect performed the preservation.
A 1902 tower on one of Broadway's triangular leftovers, its shape dictated entirely by the site. It was not the tallest building in the city and was never intended to be. Its fame comes from being photogenic from every angle, which is a consequence of the grid collision rather than of architectural ambition.
A free commuter service running past the Statue of Liberty roughly every half hour, carrying tens of thousands of people a day. It is public transport rather than a tour, and it costs nothing. It is the only free way to get a close view of the harbour that most visitors pay for.
Olmsted and Vaux's second park, in Brooklyn, and the one they considered better than Central Park. They had learned from the first: fewer constraints, a single continuous meadow, and a design not forced to work around a reservoir. It is markedly less crowded and the locals prefer it, which is not a coincidence.
Manhattan's grid was drawn on farmland before the city got there.
The Commissioners' Plan of 1811 covered everything from Houston Street to 155th, laid across valleys, streams and two existing villages. Blocks were made uniform without regard to hills or to the people who owned the land.
Broadway is a diagonal because it was there first.
It was an existing road and was not part of the 1811 plan. Where it cuts across the new right angles it leaves triangular remainders, and those remainders became Times Square, Union Square, Madison Square and the site of the Flatiron.
Central Park was built on top of a village the city erased.
Seneca Village, a community of largely African American property owners, stood on part of the site and was removed by eminent domain in the 1850s. It was left out of the park's history for well over a century.
Grand Central's ceiling sky is backwards.
The painted constellations are reversed. Explanations have ranged from a straightforward mistake in transferring a design to the claim that it depicts the heavens as seen from outside, looking in, which is a generous reading of an error.
The Brooklyn Bridge was finished by a woman with no formal engineering title.
John Roebling died before construction; his son Washington was disabled by caisson disease. Emily Warren Roebling learned the engineering, managed the site and dealt with the trustees for years. She was never the bridge's engineer of record.
The city's most-photographed park sits on a rail viaduct that was going to be torn down.
The High Line was an abandoned freight viaduct that had carried no trains since 1980 and was slated to be torn down. It reopened as public space from 2009 and has since driven measurable increases in surrounding property values.
Grand Central pays for itself by selling the sky.
Its tracks were buried on two levels so the land above the yards could be leased and developed. Park Avenue runs on top of the railway. The station's economics depended on the air rights the burial created.
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