Sleepy Hollow is a village in the town of Mount Pleasant, in Westchester County, New York. The village is located on the east bank of the Hudson River, about 30 miles (48 km) north of 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 2010 census was 9,870.Originally incorporated as North Tarrytown in the late 19th century, in 1996 the village officially adopted the traditional name for the area. The village is known internationally through "The Legend of Sleepy Hollow", an 1820 short story about the local area and its infamous specter, the Headless Horseman, written by Washington Irving, who lived in Tarrytown and is buried in Sleepy Hollow Cemetery. Owing to this story, 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".. Paradoxically, Sleepy Hollow has also been designated "the safest small 'city' [i.e., under 100,000 residents] in America".The village is home to the Philipsburg Manor House and the Old Dutch Church of Sleepy Hollow, as well as the Sleepy Hollow Cemetery, where in addition to Irving, numerous other notable people are buried.

Nyack ( (listen)) is a village located primarily in the town of Orangetown in Rockland County, New York, United States. Incorporated in 1872, it retains a very small western section in Clarkstown. It is a suburb of New York City lying approximately 15 miles (24 km) north of the Manhattan boundary near the west bank of the Hudson River, situated north of South Nyack, east of Central Nyack, south of Upper Nyack, and southeast of Valley Cottage.Nyack had a population of 6,765 as of the 2010 census.

Westchester County is located in the U.S. state of New York. It is the seventh most populated county in New York and the most populated north of New York City. According to the 2020 U.S. census, the county had a population of 1,004,457. Situated in the Hudson Valley, Westchester covers an area of 450 square miles (1,200 km2), consisting of six cities, 19 towns, and 23 villages. Established in 1683, Westchester was named after the city of Chester, England. The county seat is the city of White Plains, while the most populous municipality in the county is the city of Yonkers, with an estimated 199,663 residents in 2018. The annual per capita income for Westchester was $67,813 in 2011. The 2011 median household income of $77,006 was the fifth highest in New York (after Nassau, Putnam, Suffolk, and Rockland counties) and the 47th highest in the United States. By 2014, the county's median household income had risen to $83,422. Westchester County ranks second in the state after New York County for median income per person, with a higher concentration of incomes in smaller households. Simultaneously, Westchester County had the highest property taxes of any county in the United States in 2013.Westchester County is one of the centrally located counties within the New York metropolitan area. The county is positioned with New York City, plus Nassau and Suffolk counties (on Long Island, across Long Island Sound), to its south; Putnam County to its north; Fairfield County, Connecticut to its east; and Rockland County and Bergen County, New Jersey across the Hudson River to the west. Westchester was the first suburban area of its scale in the world to develop, due mostly to the upper-middle-class development of entire communities in the late 19th century and the subsequent rapid population growth. Because of Westchester's numerous road and mass transit connections to New York City, as well as its shared border with the Bronx, the 20th and 21st centuries have seen much of the county, particularly the southern portion, become nearly as densely developed as New York City itself.

White Plains is a city in Westchester County, New York, United States, and the eleventh-largest city in the state. An inner suburb of New York City, it is the county seat and commercial hub of Westchester, a densely populated suburban county that is home to approximately one million people. White Plains is located in south-central Westchester, with its downtown (Mamaroneck Avenue) 25 miles (40 km) north of Midtown Manhattan. As of 2013, the city's total population was estimated to be 57,866, up from 53,077 at the 2010 census. According to the city government, the daytime weekday population is estimated at 250,000. The city was ranked third in the top 10 places to live in New York for 2014, according to national online real estate brokerage Movoto.