Dutch settlers colonized present-day New York (then called New Netherland) in 1624, after Dutch explorer Henry Hudson discovered that the area, with its navigable rivers and natural resources, could become a lucrative colony for trade in goods and slaves. The colonists fought wars with the Manhattan Indians, from whom they infamously purchased Manhattan Island, and with the English, who sought control of the region, from 1626 to 1664. New York came under British control in 1664 but retained a significant Dutch population, especially in more remote regions like Sleepy Hollow.

Irving alludes to the Dutch colonization and culture of New York frequently. When describing Sleepy Hollow’s dreamlike atmosphere, he writes that these characteristics stem from “the peculiar character of its inhabitants, who are descendants from the original Dutch settlers” (3). He refers to Sleepy Hollow as one of the “little retired Dutch valleys […] in the great State of New York, [where] population, manners, and customs remain fixed” (8). He characterizes one of Ichabod’s students as a “Dutch urchin” (12), the women who tell ghost stories as “old Dutch wives” (20), and Van Tassel as a “Dutch farmer” (24). The narrator makes many more references to the Dutch-ness of Sleepy Hollow.