In the early 17th century, Pound Ridge was inhabited by Native Americans who spoke the Munsee language[4] and were members of the Wappinger Confederacy.

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.

[5] 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.

Shortly after the battle, four Wappinger Confederacy sachems arrived in the New England settlement of Stamford to sue for peace.

[9][10]: 17  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.

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.

After a lengthy legal battle, clear title to the 3,000 acres (1,200 ha) was finally given to Van Cortlandt heirs in 1788.

In 1815, Samuel Piatt (Peatt) (1773–1850) purchased 7 acres (2.8 ha) and an existing house from Gen. Philip Van Cortlandt.

On July 2, 1779, a force of 300 American rebels was attacked by 200 British soldiers under the command of Banastre 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.

The light horse detachment had been under the temporary command of Major Benjamin Tallmadge until the day before the attack when Colonel Sheldon arrived.

The British force consisted of 200 mounted light dragoons and infantry and included some Hessian Jagers.

The British burned the Presbyterian Church and the home of Major Lockwood before withdrawing with prisoners, cattle, arms, equipment and the battle standard of Sheldon's 2nd Regiment[12] back along the northern road to Bedford.

The British abandoned the cattle in Bedford before returning to the Bronx River camp under pursuit by the Americans as far as North Castle.

In the course of the raid the British had managed to capture some of Benjamin Tallmadge's papers including a letter from George Washington.

Pound Ridge held a number of Loyalists as prisoners or under house arrest throughout the war.

Later in the war Loyalists were denied freedom of speech, lost the use of the courts, were prevented from practicing their trades and had their property confiscated.

During this period Pound Ridge was an agricultural community in which families raised a variety of crops for their own consumption.

The decline of basketmaking in Pound Ridge was caused by a combination of competition from foreign and machine-made products as well as the collapse of the oyster industry in the Sound due to environmental pollution.

The former supervisor sold his Pound Ridge house in 1871 and moved to White Plains where he died three years later.

Three ponds were joined to create Trinity Lake which reached a capacity of 450 million gallons when the dam height was increased in 1895.

In 1891, the Stamford Water Company purchased additional land and created Siscowit Reservoir with a capacity of 88 million gallons.

[13] Annual farmers' picnics were held on the eastern shore of Trinity Lake for about 20 years from 1886 onwards.

In 1916, the Northern Westchester District Nursing Association requested permission to open a Polio hospital in Pound Ridge.

Workers improved roads and built bridges, planted trees and constructed shelters, picnic areas, walls, latrines and a museum.

Older children take the bus to the Fox Lane Campus in Bedford, where the middle and high schools are located.