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There is IIRC a Tolkien illustration of Gondolin- a circular walled city atop a flattened hill, rather like Carcasonne but more geometric, and with a very tall central watchtower, presumably that of Turgon's palace. (Tolkien liked his tall central towers).
Lake Town in The Hobbit had, if not a drawbridge, then a wooden bridge of sufficiently light construction to be torn down before Smaug arrived.
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The entire plot of The Lord of the Rings could be said to turn on what Sauron didn’t know, and when he didn’t know it.
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