Rye is the oldest permanent settlement in Westchester County. It began in 1660 when Peter Disbrow, John Coe and Thomas Studwell came from Greenwich with a small group of settlers. They were joined by John Budd the following year. Their first treaty with the Mohegan Indians gave them the land between Milton Point and the Byram River (Peningoe Neck); then the mile-long "Manussing" Island. Within several years their combined purchases comprised all of what is now the City of Rye, Town of Rye, Harrison, White Plains, parts of Greenwich, North Castle, and Mamaroneck.

In 1665, Connecticut merged these settlements under the name of Rye after ancestors in Rye, England. The New York State Legislature officially established the Town of Rye boundaries in 1788.

Today, the City of Rye is a unique blending of the old and the new. Now a residential, suburban community with every facility for modern living, it still retains its traditional atmosphere of tranquil village life as well as many historic landmarks that bind it to its three-hundred year history.

Any description of the Rye scene is incomplete without mention of its historical landmarks. The original home site and burial place of John Jay, first chief justice of the United States, is located here. Original milestone, fixed by Benjamin Franklin along the Post Road in 1763, still mark the 24th, 25th, and 26th miles from New York.

The historic Square House, built in the 1700’s, is now a museum. As a public inn for nearly a century, it housed such distinguished stagecoach riders as George Washington, John Adams, and General Lafayette. It later became Rye’s first post office and from 1904 till 1964 served as Village Hall, then City Hall.

On Milton Road, first site of community development, is the oldest house in Rye - the Timothy-Knapp house, built in the 1660’s; the Milton and Purdy cemeteries with gravestones of two centuries ago; the original Milton district school house, built in 1830, now a residence; and number 51, a colonial building dating back to 1788, currently the Rye Arts Center.