Pound Ridge was originally home to communities of the Wappinger Confederacy. The town’s name is believed to come from an Indigenous “pound,” or game enclosure, once located on one of the area’s many ridges. In the 1640s, European colonial expansion began to reshape the region, including land transactions by English Captain Nathaniel Turner and the spread of Kieft’s War into nearby areas. European settlers established a lasting presence in the early 1700s, and Pound Ridge was officially incorporated in 1788. After years of debate over spelling, the Town Board formally adopted “Pound Ridge” as two words in 1948.

On July 2, 1779, Pound Ridge became the site of a major Revolutionary War raid led by British Lt. Col. Banastre Tarleton. Local defenders included militia under Major Ebenezer Lockwood and Continental Light Dragoons led by Lt. Col. Elisha Shelton in the Hamlet area. Tarleton’s force held a strong numerical advantage, but delays in finding the route to Pound Ridge gave American forces time to prepare. Fighting was intense, and much of the town was plundered and burned before American reinforcements arrived. Tarleton eventually withdrew, leaving Pound Ridge marked by one of the war’s most dramatic local battles.

After the Revolution, Pound Ridge rebuilt its economy through agriculture, local trade, and small-scale industry. Sawmills, gristmills, blacksmith shops, and general stores helped anchor daily life, and by 1850 the population had grown to 1,486. While dairy farming remained central, the town also became known for hat making, shoemaking, and especially basket making, a craft with deep Indigenous roots in the region. Scotts Corners was widely known as “Basket Town,” and Pound Ridge baskets were prized by oyster fishermen along Long Island Sound. Together, these trades helped shape the town’s economy and identity throughout the 19th century.

One of Pound Ridge’s most memorable figures was the Leatherman, a gentle, mysterious wanderer who traveled through the region for decades in the late 1800s. Known for his handmade patchwork leather clothing, hat, and clogs, he lived in caves and rock shelters and accepted food or scraps of leather from local residents.

Though many details of his life remain uncertain, his story has become part of local folklore, and his headstone identifies him as Jules Bourglay of Lyons, France.