RYE, N.Y. -- The history of Rye dates back to 1659, when the settlers of Greenwich, moved toward Rye. One of the earliest building in Rye, dating back to 1878, is the Union Free School that still sits on School Street.
Back in 1915 and 1917 children were taught typing and carpentry in the school. In 1925, the Union Free School became Rye High School and then in 1938, as the population grew, it became Rye Grammar School.
Rye was named after the town of Rye, England. It is the oldest settlement in Westchester County, dating back to 1660. John Coe, Thomas Studwell and John Budd founded Greenwich in 1649, and 10 years later were some of the early settlers in Rye.
Between the Rye-Oyster Bay ferry (1739) and the New York-Boston stagecoach (1772) travelers used the Square House (One Purchase Street), a former Inn, to sleep over. The Square House is a few doors down from Arcade booksellers. George Washington, John Adams and Samuel Adams stayed there when they traveled to New England. Once the Rye to New York steamboat service started and the completion of the New Haven Railroad (mid 1800’s), Rye became a popular summer resort. Horseracing on “The Flats” (Rye Beach) was a special attraction for the summer visitors.