Pound Ridge is a town in Westchester County, New York, United States. The population was 5,082 at the 2020 census. The town is located toward the eastern end of the county, bordered to the north and east by the town of Lewisboro, by Stamford, Connecticut, and New Canaan, Connecticut, to the south, Bedford, New York, and North Castle to the west.

In the early 17th century, Pound Ridge was inhabited by Native Americans who spoke the Munsee language and were members of the Wappinger Confederacy. The geographical boundaries of the tribes within the Confederacy are unclear. Pound Ridge has been variously listed as within the territory of the Kitchawong, Siwanoy, and Tankiteke bands.

The Siwanoy are generally agreed to have lived along the north Long Island Sound Coast with a maximum range extending from Hell Gate to the Five Mile River separating today's Darien, Connecticut, from Rowayton to its east. The Tankiteke appear to have occupied easternmost Westchester County above the coast but extending further west in the northern part of the county and into southern and eastern Putnam County, and eastward in Fairfield County to the Saugatuck River in Westport. The territory of the Kitchawong is thought to have extended from the Croton River to Anthony's Nose along the Hudson and some distance east from the river.

The Wappinger Confederacy participated in Kieft's War which began in 1640 as a result of escalating tensions over land use, livestock control, trade and taxation between the Dutch West India Company colony of New Netherland and neighboring native peoples. In March 1644, a Wappinger Confederacy village in present-day Pound Ridge was attacked by a mixed force of 130 New Netherland soldiers under the command of John Underhill. This event is now known as the Pound Ridge Massacre. The soldiers surrounded and burnt the village in a night attack killing between 500 and 700 Indians. The dead included 25 members of the Wappinger tribe, with the remainder being either Tankiteke or Siwanoy or both. The New Netherland force lost one man killed and 15 wounded. More casualties were suffered in this attack than in any other single incident in the war. Shortly after the battle, four Wappinger Confederacy sachems arrived in the New England settlement of Stamford to sue for peace.

The territory of modern Pound Ridge was first permanently settled by Europeans in 1718 in the present-day Long Ridge Road area. Long Ridge Road was originally an Indian path and had been used by the first settlers of Bedford, New York, as they traveled to that destination from Stamford. Although the very first settlers were from Huntington on Long Island, most of the original settlers of Pound Ridge were from Stamford. A large portion of Pound Ridge was included in the town of North Castle when it was incorporated in 1721.

Three thousand acres in the northern part of present-day Pound Ridge were included within the more than 86,000-acre (35,000 ha) Cortlandt Manor grant which extended from the Hudson River in the west 20 miles (32 km) east to the Connecticut border. A member of the historically prominent Lockwood family first purchased land in Pound Ridge in 1737 and several members of the family settled in the town within the next six years. The Scofield family first settled in the area in 1745 and the first Fancher settled in the area in 1758. Roads in the modern town bear the name of each of these families. The first record of the term "Old Pound Ridge" to refer to the present-day town's territory is found in the North Castle records from 1737. "Old Pound Ridge" begins to appear in Stamford records in 1750. The name "Old Pound Ridge" is thought to have originated from the presence of an Indian game pound on a hill within the territory when the settlers first arrived.^{[citation needed]}

During the 1700s, the Boutonville area of Pound Ridge found itself at the center of a 50-year land dispute concerning overlapping grants of the Van Cortlandt Manor grant to Stephanus Van Cortlandt and to the Stamford patentees. After a lengthy legal battle, clear title to the 3,000 acres (1,200 ha) was finally given to Van Cortlandt heirs in 1788. Most of this land is now part of the Ward Pound Ridge Reservation. Sometime after that, Pierre Van Cortlandt built a home there. In 1815, Samuel Piatt (Peatt) (1773–1850) purchased 7 acres (2.8 ha) and an existing house from Gen. Philip Van Cortlandt. This home, since demolished, was on what now is Honey Hollow Road. The farmland in the Pound Ridge and Lewisboro sections (Ward Pound Ridge Reservation) were part of the Van Cortlandt Manor lands that were divided into "great lots" of about 3,000 acres (1,200 ha) each. These lots were further divided into 300-acre (120 ha) farms.

Pound Ridge was the site of a battle during the American Revolutionary War. On July 2, 1779, a force of 300 American rebels was attacked by 200 British soldiers under the command of Banastre Tarleton. The raid was the first independent command for the 24-year-old Tarleton. The attack was planned as one of a series of raids on rebel forces in the region, the purpose of which were to draw Washington's army away from the Hudson River.