At the southern end of Upstate New York is the Lower Hudson Valley. It is a region of blended histories for its European settlers and their descendants, beginning with its initial exploration by Englishman Henry Hudson on behalf of the Dutch East India Company in 1609. Even after the English acquisition of New Netherland in 1664 and the formation of the United States in 1776, the regional population long remained predominantly Dutch. In the wider public imagination, the region’s Westchester County is especially notable due to the literary contributions of American writer Washington Irving (1783-1859).

Irving is renowned nationally and internationally for his short stories Rip Van Winkle (1819) and The Legend of Sleepy Hollow (1820), which were featured in the collection The Sketchbook of Geoffrey Crayon, Gent. The Legend is the longest story of The Sketchbook, fundamentally influenced by the cultural-religious histories of what are today the modern Villages of Sleepy Hollow and Tarrytown in Westchester. Although The Legend became synonymous with hauntings and the supernatural, its themes also vitally consider the temporal, primal tensions found between homogeneity and the outsider as well as between tradition and change.

Irving’s life was spent in and out of both New York and the United States, but his initial, formative visit to Tarrytown, to escape a yellow fever outbreak in New York City, was as a teenager in 1798. Tarrytown was already a formal Village at the time, but the northern area where the Pocantico and Hudson Rivers meet was only colloquially known as Slapers Haben (Sleepers Haven), a name first given by Adrien van der Donck (1618–55). “Sleepy Hollow” was only popularized, and further formalized, much later because of The Legend. Three historic churches in Sleepy Hollow and Tarrytown exemplify the seminal intertwining and proliferation, via Irving, of local culture into universal literature.