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Greylock is famous as part of Melville's inspiration for "Moby Dick" having the peculiar property of looking rather like the outline of a whale from Arrowhead, his Pittsfield home; nowhere else does Greylock resemble a whale, through the landslide on the Adams side of the mountain does resemble the head of an American Indian, and is popularly termed "Chief Greylock".
In Harry Potter canon, the American School of Wizardry, [https://harrypotter.fandom.com/wiki/Ilvermorny_School_of_Witchcraft_and_Wizardry Ilvermorny], is on the top of Greylock.