Long before European settlement, the Hudson Valley was home to Indigenous peoples including Munsee-speaking Lenape communities. The river and surrounding woodlands supported fishing, agriculture, travel, and trade. Like much of the lower Hudson region, the area was transformed by Dutch colonial settlement in the 17th century.
The settlement that became Sleepy Hollow developed as part of New Netherland and later English colonial New York. One of the area's most important early landmarks is the Old Dutch Church of Sleepy Hollow, built in the late 17th century and closely associated with the Philipsburg Manor estate. The manor was part of a large patroon-like landholding worked in significant part by enslaved Africans, an essential but often underemphasized part of the region's colonial history.
During the American Revolutionary War, the lower Hudson Valley was a strategically contested zone. The nearby broad area around Tarrytown and the Hudson crossing points saw troop movement, espionage, and military tension. The capture of British Major John André in nearby Tarrytown in 1780 became one of the best-known local events of the war.
In the early 19th century, Washington Irving gave the area global cultural significance. His *The Legend of Sleepy Hollow* and other writings drew on local landscapes, folklore, and Dutch-descended communities along the river. Over time, the fictionalized Sleepy Hollow became inseparable from the real place.
The municipality was incorporated in 1874 as the Village of North Tarrytown. Through the late 19th and 20th centuries, the village developed as a mixed residential and industrial community tied to the river, rail transportation, and manufacturing. Its most prominent industrial employer became the General Motors assembly plant, which for decades shaped the local economy and working-class life.
After the GM plant closed in the 1990s, the village entered a period of economic transition. In 1996, residents voted to rename North Tarrytown as Sleepy Hollow, emphasizing heritage and tourism while retaining its role as a residential community. In recent decades, large waterfront redevelopment projects, adaptive reuse, and heritage tourism have changed the local landscape, while the village has continued to reflect the broader demographic diversity of Westchester County.
