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Boston (https://www.google.com/maps/@42.3591352,-71.06249,15.28z) is close to round. You don't get grids until you get out of the colonial era city.

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These cities were originally part of the colonies of the British empire. So I would say they aren't necessarily completely "American". I'd look more central to western US cities to see how American style city planning is done.

What you have are different eras. Older is usually more chaotic. Look at New York below 14th St., then contrast with above which came later.

You can draw another line when car culture became common. Before then, it was grids accessible by streetcars. After, the cul de sac style and similar becomes common.

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