How it All Began

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.

Revolutionary Wartime

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.

Rebuilding and Trade

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.

Preservation

Preservation remains one of Pound Ridge’s defining values. Historic homes, civic buildings, stone walls, and old roads are part of the town’s everyday landscape and give residents a strong sense of continuity and pride of place. Efforts to identify, document, and landmark significant houses have helped protect the town’s architectural heritage, while land preservation, conservation-minded planning, and protected open space have preserved the rural setting that gives these places their meaning. As of the 2020 U.S. Census, Pound Ridge had 5,082 residents, most living in single-family homes. The result is a town where historic character and natural habitat still coexist, with deer, foxes, coyotes, bobcats, waterfowl, and many other species remaining part of daily life.

Midcentury Modern

Pound Ridge’s modern architectural story began in the late 1930s and accelerated through the 1950s and 1960s, when architects, artists, and families from New York brought new design ideas into the town’s wooded landscape. Early and mid-century houses by architects including John C.B. Moore and David Henken introduced flat or low-pitched roofs, broad walls of glass, open plans, and strong indoor-outdoor connections.

That tradition continued and evolved in later decades through the work of Vuko Tashkovich, who developed a more sculptural and highly individual architectural language while keeping a core modern principle at the center: designing homes in conversation with the land, light, and surrounding trees.

Midcentury Modern houses in Pound Ridge emphasized low or gently pitched roofs, large expanses of glass, open and efficient floor plans, deep overhangs for seasonal light control, and a strong visual connection to the land. Rather than treating buildings as isolated objects, many designs were carefully integrated with rocks, trees, and natural grade. From custom family projects to architect-designed residences linked to major modernist circles, Pound Ridge’s mid-century homes helped define the town’s character and continue to shape its identity today.

Hiram Halle and the Community

Hiram Halle is probably Pound Ridge's biggest benefactor. A successful businessman and inventor, he helped found the University in Exile at the New School for Social Research which rescued Jewish scholars, academics and artists from Europe during the Holocaust. Halle moved to Pound Ridge in 1929. He hoped to enhance the community via his philanthropy and his work restoring homes in the community. Benny Goodman was another resident and he even composed a melody entitled "Pound Ridge". By the 1940's, Pound Ridge's population rose to almost 800, and it continued to grow slowly and steadily to 4,000 in 1980 and 4,550 in 1990.

Early 20th Century Economy

By the early 20th century, farming had declined as had the cottage industries. The railroads in Westchester, which opened up markets and brought in new people, bypassed Pound Ridge. By 1920, the population dwindled to 515. Then, during the 1930s things changed. Hiram Halle, an inventor and businessman, came to Pound Ridge from New York City and began renovating and reconstructing houses.

Pound Ridge Today

Located in the northeast section of Westchester County, the municipality of Pound Ridge borders both New York and Connecticut. Pound Ridge is adjacent to the Connecticut towns of New Canaan and Stamford. On the New York side, Pound Ridge borders Bedford and the more rural town of South Salem. Pound Ridge is characterized by a rugged landscape, rock outcroppings and rugged cliffs. "Nowhere in the town's 23 square miles is there even a traffic light."

In many parts of Pound Ridge, the rugged landscape seems to have been only gently altered by humans since the glaciers receded. In contrast to some of its neighbors, the town, Westchester's smallest in population density, has marked its topography over the years not with highways and malls but rather with stone walls and narrow country roads that wind past meandering brooks, stone outcroppings and densely wooded hills. Pound Ridge boasts many large tracts of conserved and undeveloped land. Between the 4,315 acre Ward Pound Ridge Reservation, the efforts of the Westchester Land Trust and the Pound Ridge Land Conservancy combined with sensitive town planning, much of Pound Ridge will remain "forever wild."    

The Leatherman

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.