The Town of Rye includes the villages of Rye, Port Chester, and Rye Brook, and is surrounded the Byram River and Long Island Sound, providing a picturesque panorama. Several major highways make Rye easily accessible to Connecticut and all points north, as well as New York City.
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. In 1683, Rye was ceded unwillingly to the Province of New York by King Charles II as a gift to his brother, the Duke of York. But when a New York court severed the Harrison area from the settlement in 1695, the Rye colonists rejoined Connecticut in protest. In 1700, Rye again became part of New York by royal decree, this time permanently. The New York State Legislature officially established the Town of Rye boundaries in 1788. For two centuries, Rye remained a secluded community. Land was cleared for farming and cattle grazing. Docks were built on Long Island Sound, and oystering was an important occupation. Homes along Mill Town Road, now Milton, led to grist mills on Blind Brook.
In the late nineteenth century, Rye experienced its first real growth and change. The era of the trolley made surrounding communities accessible. By 1904, there were two schools, five churches, a library, and a lively population of 3,500 residents. As Rye developed, the residents began to desire complete independence from the Town government. City status offered many advantages, one being relief from paying a disproportionate share of the Town welfare tax. In 1940, the Legislature approved the Rye City Charter which was adopted by the residents 1,172 to 34. On January 1, 1942, Rye became Westchester’s sixth and smallest city.
Playland’s opened in 1928 and offered a waterfront area along the Long Island Sound. It was also a site of growing collection of recreational developments, including hotels, resorts and “amusement areas.” The original design included a boardwalk, ice-skating rinks, a swimming pool, and two beaches as well as amusement park rides. Some of those amusement park rides, such as the Dragon Coaster that serves as the park’s mascot, are still in use. The Dragon Coaster is one of roughly 100 wooden roller coasters still in operation in the United States. In 1987, Playland was declared a National Historic Landmark.
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. Rye is primarily a place in which to live rather than to make a living. One-third of Rye’s working residents commute to New York City, 25 railroad miles away. Others are employed in Westchester, Connecticut, New Jersey, and Long Island as well as in the 200 small businesses and several large firms located here.
The Village of Rye maintains the feel of a quaint New England town, while at the same time, offering everything to the resident in the way of modern amenities. Its charming downtown is home to an eclectic mix of small shops, upscale eateries, as well as the Metro North station, providing convenient service for Manhattan commuters and weekend travelers. Beautiful, residential neighborhoods blend with estates to make this area so attractive.
The Rye City School District includes three National Blue Ribbon elementary schools of Excellence serving grades K-5. Rye Middle School, also a National Blue Ribbon School of Excellence, serves students grades 6-8, and Rye High School, ranked among the top high schools in the country by U.S. News and World Report and Newsweek Magazine, provides a full range of curriculum opportunities at Regents, honors and Advanced Placement levels for ninth through twelfth graders. The Rye School of Leadership, part of Rye High School, serves high school students who learn best in a non-traditional educational environment. The mission of the Rye City School District, in partnership with the community, is to ensure that every student is capable of becoming a life-long learner who can thrive in a global environment as a self-reliant and socially responsible citizen.