Sleepy Hollow is a village in the town of Mount Pleasant in Westchester County, New York, United States, in the New York metropolitan area.
The village is located on the east bank of the Hudson River, approximately north of Midtown Manhattan in New York City, and is served by the Philipse Manor stop on the Metro-North Hudson Line. To the south of Sleepy Hollow is the village of Tarrytown, and to the north and east are unincorporated parts of Mount Pleasant. The population of the village at the 2020 census was 9,986.
Originally incorporated as North Tarrytown in the late 19th century as a way to draft off Tarrytown's success during the Industrial Revolution, the village adopted its current name in 1996, some three and a half centuries after the first Dutch settlers called the area "Slapershaven" or "Sleepers' Harbor."
The village is known internationally through The Legend of Sleepy Hollow, an 1820 short story by Washington Irving about the local area and its infamous specter, the Headless Horseman. Irving lived in the area and is buried in Sleepy Hollow Cemetery, where numerous other notable people are buried, while real-life inspirations for his characters are interred in the adjacent Old Dutch Burying Ground.
Owing to The Legend, as well as the village's roots in early American history and folklore, Sleepy Hollow is considered by some to be one of the "most haunted places in the world". Despite this designation, Sleepy Hollow has also been called "one of the safest places to live in the United States". Today, the village "thrives as a symbol of Americana, drawing tens of thousands each fall to its haunted hayrides, lantern-lit cemetery tours, pumpkin festivals, and theatrical reimaginings of Irving’s famous tale."
History
The two square miles of land that would become Sleepy Hollow belonged to the larger domain of the Wecquaesgeek, a Munsee-speaking band of Wappinger people. Their fort and burying ground may have been located on the hillside where the Old Dutch Church of Sleepy Hollow was to be built later. In 1609, Henry Hudson claimed the Hudson Valley, including the Tappan Zee area, for the Netherlands. There was relative peace between the Native Americans and the Dutch until the mid-17th century, and the Dutch West India Company had been providing its investors with large land grants called patroonships to encourage settlement of the New Netherland colony on lands bought from local Native American tribes along the East Coast of what is now the United States.
The Upper Mills
Much of the land that would become Philipsburg Manor had previously belonged to Adriaen van der Donck, who had invested in such a patroonship before the English conquest of New Netherland in 1664. In 1672, merchants Frederick Philipse (or Vredryk Flypse),Chronicles of Tarrytown and Sleepy Hollow by Edgar Mayhew Bacon. The Knickerbocker Press. (1900), p. 5. Thomas Delavall, and Thomas Lewis purchased from his widow's brother the first tracts of land in current-day northern Yonkers.Maika, Dennis J. (2005). "Philipsburg Manor". Encyclopedia of the State of New York, First ed. (Peter Eisenstadt, ed.). Syracuse, New York: Syracuse University Press. p. 1199. Philipse made several additional purchases between 1680 and 1686 from the Wecquaesgeek and Sintsink tribes, expanding the property to both the north and south. Philipse also bought out his partners' stakes during this time, enticing friends from New Amsterdam and Long Island to move with him with the promise of free land and limited taxes. The manor grew to around 52,000 acres (21,000 ha) or about 81 sq mi (210 km2), comprising much of today's lower Westchester County. Philipse was granted a royal charter in 1693, creating the Manor of Philipsburg and establishing him as first lord of the manor.
Philipse founded his country seat at the mouth of the Pocantico River, in the northern part of his manor, which would be called the Upper Mills. A small Dutch community had already been established there when he arrived in 1683. He built a gristmillAccording to the village historian Henry Steiner, it has been suggested there may have been an even earlier mill and pond on this site. (Steiner, Henry (1998) The Place Names of Historic Sleepy Hollow & Tarrytown. Heritage Books, p. 84) and shipping depot, today part of the Philipse Manor House historic site. A pious man (and a carpenter by trade), he was architect and financier of the settlement's stone church, known today as the Old Dutch Church of Sleepy Hollow, and was said to have built the pulpit with his own hands.Edited Appletons Encyclopedia, Famous Americans: Biography of Frederick Philipse: "...He worked at the carpenter's trade for several years, aided in building the Old Dutch church, and is said to have made the pulpit with his own hands. The church served successive lords and ladies of the manor and their tenant farmers (who were largely Dutch, French Huguenot, Swiss, and German immigrantsTenant farmers' houses had been on their small plots spread across the massive estate. They paid their rent in part by the grain they produced and were bound to bring all their grain to the Upper Mills gristmill for grinding.) until the outbreak of the American Revolutionary War.
When Philipse died in 1702, the manor was divided between his son, Adolphus Philipse, and his grandson, Frederick Philipse II. Adolphus received the Upper Mills property, which extended from Dobbs Ferry to the Croton River. Frederick II was given the Lower Mills at the confluence of the Saw Mill and Hudson Rivers. Adolphus transformed the Upper Mills into a major commercial operation and managed it for nearly 50 years. The complex then included a stone gristmill, a bakehouse, workshops for blacksmiths, carpenters, and coopers, and a wharf for exporting grain and cornmeal internationally and for importing foreign goods. It was surrounded by fields of grain, orchards, stands of timber, and stone quarries. The complex was largely operated by enslaved Africans. Slave quarters were installed by Adolphus about 90 feet from the main house. By the time of his death, twenty-three enslaved men, women, and children lived and worked at the manor. They are catalogued by name (and children, also with ages) in the 1750 probate inventory of his properties. As the most valuable "chattel" (personal property), they are listed first - before cattle, furniture, and tools.
Adolphus's nephew, Frederick Philipse III, became the third lord of the manor upon his uncle's death. He did not live at the modest Upper Mills house, choosing the manor house at the Lower Mills (now Philipse Manor Hall State Historic Site) as his primary country estate and developing it into a grand Georgian-style mansion suitable for a man of his status.In the late 18th century, the Lower Mills area was often referred to as "Philipse's." The Upper Mills main house, gristmill, surrounding buildings, ponds, fields, woods, and a wharf on the Hudson River (that is, everything related to the large-scale production and sale of flour, dairy products, timber, and other goods) were leased by Philipse to members of prominent local landowning families, first Josiah MartlingThe Martlings were early Dutch settlers and influential members of the area community. One of the Martling family members, blacksmith Abraham Martling, is believed to be the historical inspiration for the character Brom Bones in The Legend of Sleepy Hollow. His grave in the Old Dutch Burying Ground is located just several feet away from that of Catriena Ecker Van Tassel, whose name Irving borrowed for Katrina Van Tassel.
Names of several Martling family members are engraved on the Revolutionary Soldiers' Monument in the adjacent Sleepy Hollow Cemetery. (from 1752 to 1761) and then William PugsleyWilliam Pugsley came from a large Westchester Quaker family associated with, among other things, Pugsley Park in Peekskill, Pugsley House in Ossining, Pugsley Hollow inNew Rochelle, and Pugsley Avenue in The Bronx. He died in 1786, shortly after he sold his lease to Beekman, and is buried in the Old Dutch Burying Ground. Many of his relatives were Loyalists, who joined the "Loyalist exodus" to Canada after the British defeat in the American Revolution. There, they and other refugees from New England and New York founded the community of Philipsburg, Quebec. Premier of Canada’s province of New Brunswick, William Pugsley, was a descendant of theirs. (from 1761 till after the American Revolutionary War). It is the area of this leaseholding that would become the core of the present-day village of Sleepy Hollow.
During the American Revolutionary War, the Upper Mills area was situated within the Neutral Ground, an unprotected buffer zone between British-controlled territory to the south and American lines to the north. Numerous local histories and scholarly articles document the hardships faced by residents in the neutral ground, who were subjected to devastating raids from both sides. Their level of desperation is well illustrated by the oft-quoted description, “They feared everybody whom they saw.” Knowing the terrain well, many local residents served as crucial scouts, guides, and foragers for the Continental Army in the infamous neutral ground. The Old Dutch Burying Ground, the area's oldest cemetery, holds one of the highest concentrations of Revolutionary War veteran graves in the state of New York.
In the late 1790s, Washington Irving visited the Sleepy Hollow area with his local friend James K. Paulding, a Revolutionary War militiaman who in 1780 had helped capture British Major John André in what is now known as Patriot's Park and thereby foiled the plans of Benedict Arnold. Together they explored the area, hunting, fishing and talking with the local folk. The visits of Irving—and the local folklore and ghost tales he heard while there—were immortalized in the enduringly popular story The Legend of Sleepy Hollow.
The renowned writer Washington Irving's descriptive yet mystical account of Sleepy Hollow gave much of this little town its famous reputation. Irving spent a considerable amount of time in Sleepy Hollow during his teenage years to escape the yellow fever epidemic in Manhattan. In doing so, he developed a good understanding of the area and a general admiration for it.Thompson, T. W. (2024). Architecture as metaphor in Washington Irving's “The Legend of Sleepy Hollow.” ANQ: A Quarterly Journal of Short Articles, Notes and Reviews, 37(2), 189–192. https://doi.org/10.1080/0895769X.2022.2103638 By describing it as "one of the quietest places in the whole world" and frequently evoking its drowsy atmosphere in his short story The Legend of Sleepy Hollow, Washington Irving delighted readers with his depiction of the town's mysteriousness.Irving, W. (1820). The legend of Sleepy Hollow. In The Sketch Book of Geoffrey Crayon, Gent. (Original work published 1819–1820) Irving also incorporated iterations of the tales and legends he often heard during his time in Sleepy Hollow into The Legend of Sleepy Hollow, resulting in the ghostlike characters of Diedrich Knickerbocker and The Headless Horseman serving as Sleepy Hollow's hallmark.Hoffman, D. G. (1953). Irving's use of American folklore in “The Legend of Sleepy Hollow.” PMLA, 68(3), 425–435. The Legend of Sleepy Hollow enthusiasts frequently visit Sleepy Hollow during the Halloween season to this day.
Town
In 1779, Frederick Philipse III, the last lord of Philipsburg Manor and a staunch Loyalist, was attainted for treason by New York's revolutionary government. Philipsburg Manor was confiscated, split into about 300 lots, and then sold at public auction. Most of the buyers were Philipse’s tenant farmers who used the opportunity to buy the small plots they worked. A much larger Upper Mills property, about , was purchased by the New York merchant Gerard (Gerardus) Garret Beekman Jr.