The ghost of a colonial road on the eastern side of the Chrysler Building

There’s no finer example of a New York City Art Deco skyscraper than the Chrysler Building, which gleams with strength and grace 77 stories over 42nd Street and Lexington Avenue.

The Chrysler Building in 1931, rising above 42nd Street

This icon of Machine Age Manhattan was completed in record time between 1928 and 1930, in a race with 40 Wall Street to claim the title of New York’s tallest building. (The Empire State Building beat them both when it debuted on the skyline in 1931.)

Designed by William Van Alen for Walter Chrysler, the head of the car manufacturer, the building begins with a base and then features elegant setbacks as the slender tower rises higher and higher, finally coming to a crown and then a point, literally, with a stainless-steel needle spire that pierces the clouds.

The architectural loveliness of its exterior and interior deserve their own lengthy posts. This post is about how a slant along the Chrysler Building’s setback reflects the former presence of a primitive road traversed by colonial-era New Yorkers.

Gerald R. Wolfe points out this setback in his deeply researched book of walking tours, New York: A Guide to the Metropolis. “Around the corner on 42nd Street (best viewed from the south side of the street), it will be noted that the east wall of the Chrysler Building’s lower setback is not parallel to the north-south avenues,” wrote Wolfe.

This 1822 map shows 42nd Street and Eastern Post (Boston Post) Road as the road crosses Lexington and Third Avenues

Take a look when you’re in the neighborhood: you can see that this eastern setback was built on a rightward slant, while the other setback walls are straight.

What’s the explanation? It’s the ghost of Boston Post Road, a long-defunct thoroughfare and one of the city’s few reliable roadways in the 17th and early 18th centuries. (Boston Post Road was also called Eastern Post Road, or East Post Road—it was the thoroughfare to take if you were heading out of the city to New England.)

Plans for the trapezoid-shaped Chrysler Building

The plot of land on which Walter Chrysler planned to build his tower once bordered Boston Post Road, which predated the city street grid and ran roughly between today’s Third and Lexington Avenues, Wolfe explained. When he acquired it, the original border remained—even though the road was defunct.

With this meandering colonial road forming the parcel’s eastern boundary, Chrysler ended up with a slanted plot shaped like a trapezoid, as Sam Roberts put it in his 2019 book, A History of New York in 27 Buildings. Hence the angled setback, which reflects the angle of this de-mapped road.

Boston Post Road disappeared from city maps in the 19th century, though it’s unclear when. It was definitely gone by the Gilded Age: A New York Times article from 1881 describes it as “now obliterated and forgotten.”

Other ghosts of the Boston Post Road still exist though. One remnant is this East 49th Street courtyard, where travelers could catch the stagecoach to Boston.

In 1929, ready to wow the world

[Top photo: NYPL; third image: Map of the Common Lands;; fourth image:; fifth image: NYPL]

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8 Responses to “The ghost of a colonial road on the eastern side of the Chrysler Building”

  1. countrypaul Says:

    One wonders what Manhattan would have looked like had more of these thoroughfares of old been maintained. Maybe more like London? Broadway gives a hint….

    • ephemeralnewyork Says:

      Our adherence to the 1811 grid system made NYC easier to navigate, though! And then when you want to experience the early streets, there’s always downtown, the Village, and Manhattanville.

  2. seanglenn47 Says:

    Just a note that the land the Chrysler Building is on is owned by the college, Cooper Union. The owners of the Chrysler Building must pay a yearly rent on this “land lease” every year, and it supplies a significant amount of the college’s yearly budget, as the college was (but no longer is) full scholarship for it’s students.
    There is probably a very interesting story how that came to be, probably tied up in the college’s founder, industrialist, Peter Cooper.
    Glenn in Brooklyn, NY.

    • Ginny Poleman Says:

      I was going to comment on this as well. Cooper Union’s original lot probably pre-dates the grid, hence the odd shape.

    • ephemeralnewyork Says:

      Thank you for mentioning this; I tried to work it into the post but it was getting too long. Cooper Union was given the land as a donation by Andrew Carnegie and members of the Cooper and Hewitt families in 1903. The land was probably in the Cooper/Hewitt families for decades, back when Boston Post Road was part of the cityscape. So the lot reflected the presence of the colonial road.

  3. velovixen Says:

    New York, to outsiders, has a reputation as a city that erases its past. This post belies that belief.

    In a way, it makes sense that an early skyscraper would give a nod to a defunct road when you realize that some of those who commissioned, designed and built the first generation of skyscrapers were descendants (or related to those descendants) of this city’s early European settlers—or, at least, were well-read in that history.

    I know that the Boston Post Road continues through Westchester County and beyond and, if I am not mistaken, is a continuation of Boston Road in the Bronx, which was also called Boston Post Road. Are those thoroughfares continuations of the “lost” road echoed in the Chrysler Building?

    • ephemeralnewyork Says:

      Yes, the Boston Post Road in Westchester is a continuation of the Boston Post Road in the Bronx, which is the same as the road that since the 19th century has been wiped off the map in Manhattan. If you were trying to get to New England in, say, 1805, Boston Post Road was your only way out. Imagine what it was like catching the stagecoach for the trip!

      • countrypaul Says:

        Huguenot Street in New Rochelle, as well as East and West Main Streets, are that same Boston Post Road. The earlier name continues in Pelham to NR’s west and Larchmont and Mamaroneck to its east. Of course,it also persists in many Connecticut towns, too.

        A question: there must have been a ferry across the Harlem River. Any idea where and when it ran, and when a bridge replaced it?

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