Rye, NY

As Westchester County's oldest settlement, the city of Rye can trace its history back to 1660. The settlement was named for Rye, England in 1665 as part of Connecticut. In 1683, the town was ceded to New York against the settler's wishes as a gift from King Charles II to his brother, the Duke of York. The settlers rebelled and tried to rejoin Connecticut, but it was officially established as part of New York by royal decree. Today, this beautiful community is one of the nation's most expensive areas to purchase real estate with the average home selling for more than $2 million.

Rye still retains its historical charm in its architecture, stone walls, and shady narrow lanes. Rye is a harbor town, stretched along the Long Island Sound and offering one of the state's prettiest beaches -- Rye Town Park and Beach. With its Spanish-style buildings dating to around 1907, this historic park and public beach features a bath house, picnic shelters, and a restaurant dating to 1910.

Another landmark, the Square House Museum, was once a tavern and inn dating to around 1730 and serving such famous guests as George Washington, General Lafayette, and John Adams. Listed on the National Register of Historic Places, it now serves as a local history museum. The oldest house in Rye is the Timothy-Knapp House, built around 1660. The Milton Cemetery, across the street, is also on the National Register -- it was the first public burying ground in Rye. Another historic destination offers a different kind of chill from the cemetery. Playland first opened in 1928 and quickly became "America's Premier Playground" with its amusement rides and circus acts. Today, the park still features several rides built before 1930.