Evidence of Paleo-Indians in the area dates back more than 8,000 years. In more recent times, before European settlement, native peoples belonging to the Delaware Lenape culture inhabited what is now Lewisboro. By the Late Woodland Era and Contact period with the Europeans, the Tankiteke and Kitchawanc people of the Mohegan Nation farmed small plots, set up seasonal hunting camps and fished the streams.
European settlers came from two directions – east from the New Haven Colony of Connecticut and south and west from New Amsterdam and the Hudson River. In the late 1600’s, land was sold to New Haven and Norwalk colonists by Chiefs Ponus and Catoonah, often the same land; deeds can be very confusing. The first recorded settlers, William Truesdale and Samuel Tuttle, purchased land from the Ridgefield Proprietors about 1720 and attempted to put up stakes in Salem. By 1728 they had given up. Tuttle’s name has disappeared, but legend says that Truesdale was killed by Indians and his bones left on the hillside above the lake that now bears his name. However, recent research indicates Mr. Truesdale died in New Jersey.
The eastern section of town, the hamlets of Vista, Lewisboro Hamlet and South Salem, were all part of a disputed area called The Oblong. The Oblong’s western border was set at 20 miles east of the Hudson River and extended from Long Island Sound to Massachusetts. Connecticut and New York lands within this area changed hands several times before the state border was finally established in 1731; it was disputed for another century. The western section of town, including the Cross River and Goldens Bridge hamlets, was part of Cortlandt Manor, a 1697 land grant to the Van Cortlandt family by King William III. The manor lands were divided in 1732 and farms of 150 to 300 acres were sold or rented to farmers. Many of these properties became part of Lewisboro in 1788 when New York State officially established town boundaries. Waccabuc Hamlet was settled by the Mead family in the 1770’s.
1731 is taken to be the date of the town’s establishment, but the first recorded town meeting is 1747. The saga of the town’s name can be confusing! From 1731 until 1783 the town was known as Salem and included parts of North Salem; 1783 - 1806 it was Lower Salem; and from 1806 – 1840 folks lived in South Salem.
Then, in February 1840, thanks to a generous $10,000 donation for the support of public education from businessman John Lewis, whose caveat was that the town be named for him, Lewisboro became the name on the map.
The town saw little action during the American Revolution, but in 1780, Jacob Gilbert’s Salem house provided a prison for Major John Andre, co-conspirator of Benedict Arnold in the attempt to capture West Point. During his three-day imprisonment, Andre wrote to Gen. Washington revealing his identity and asking for leniency. The Main Street house is gone but a plaque commemorates the event. There was no action during ensuing wars, but Lewisboro was home to at least a couple of Cold War era spies, including Martha Dodd Stern and her husband, Alfred.
Historic points of interest include the Cross River Baptist Church (c.1790), St. John’s Episcopal Church (1855), Monument Rock on Elmwood Road, Hideout Hill, the 1940’s home of Alexander Kerensky, Russia’s first prime minister after the overthrow of the Czar; Farvue Farm, home of Henry Agard Wallace, Vice President and Secretary of Agriculture under FDR; Onatru Farm; and the following places on the National Historic Registry: Mead Chapel, Peaceable Kingdom, The South Salem Presbyterian Church Graveyard, The Homestead on Mead Street, and the Whipple Truss Railroad Bridge # L-158 in Goldens Bridge.
A History of the Town of Lewisboro, published in 1995, is available at the Lewisboro Library, 15 Main Street, South Salem, NY 10590. Other reference materials can be found in the library’s reference section.