Wandering tribes of Mohegan Indians were the earliest inhabitants of the area known today as Rye Town and the Village of Port Chester. Port Chester started as a shipping village, becoming a factory town by the 1950’s. It has recently seen a resurgence and has become known for its hub of ethnic eateries, specialty shops, and the recently developed Waterfront at Port Chester shopping and entertainment complex.
The first white settlers were a group of enterprising young men and women who came from the English colony of Connecticut in 1660. After land purchases from the Indians, negotiated mostly by Peter Disbrow, they settled on the island of "Manussing," for which they had paid "eight cotes and seven shirts fifteen fathom of womone." Although the land was part of the territory claimed by the Dutch, the defiant colonists drew up a proclamation in 1662 declaring allegiance to Charles of England. Through further treaties with the Indians, their combined holdings soon comprised all of what is now the City of Rye, Town of Rye, Harrison, White Plains and parts of Greenwich, North Castle and Mamaroneck. In 1665 the General Court of Connecticut merged the settlement under the name of Rye, in honor of a prominent family among the early colonists who has come from Rye, England.
For nearly one hundred years, Rye was disputed territory between New York and Connecticut, until finally, in 1788, the New York State legislature officially established the Town of Rye boundaries. The group of settlers moved outward from Manursing Island and eventually developed Peningo Neck (the present business section of the City of Rye) and "Saw Pit" as Port Chester was commonly called then. Saw Pit (also know as Saw Pits and Saw Pit Landing), was named for the saw-mill and boat building shop near the mouth of the Byram River where the community evolved. It was little more than a hamlet until near the Revolutionary War period. But with its good harbor and growing shipbuilding industry, the port became a natural outlet for farm produce from the surrounding countryside.
During the Revolutionary War, Saw Pit was an important military outpost. Both armies vied for possession of the port, and the village was nearly destroyed in the crossfire. In 1776, American General Israel Putnam used the Bush Homestead, in what is now John Lyon Park, as his headquarters. When the clamor of the Revolution settled, the area was rebuilt and its shipping and shipbuilding industries prospered. Before long it had become an important steamboat stop, the eastern "port of Westchester." The name Port Chester was adopted in 1837. On May 4, 1868, Port Chester was incorporated as a village with specified limits within the Town of Rye.
The decline in agriculture and shipping came during the latter half of the 19th century, with the establishment of major railroads. Gradually, the community of Port Chester changed, from a port and trading center to a manufacturing center. By 1950, Port Chester was among the leading factory towns in the Lower Hudson Valley. Many well-known corporations had headquarters or production centers in the village, including Life Savers, Empire Brush Works, Arnold Bread, Fruit of the Loom and Russell Burdsall Nut & Bolt Co. On evenings and weekends, Port Chester's downtown hummed with vitality, as residents of neighboring towns flocked to the village's stores and restaurants. During the 1970s, most of the factories began to move south or west. Like many other manufacturing communities in the Northeast, Port Chester struggled with a declining economic base. In 1984, Lifesavers shut down its North Main Street factory after 64 years, the last major manufacturer to leave the village.
Since then, Port Chester has revitalized itself with a growing retail and service economy. Port Chester's downtown Restaurant Row is renowned throughout the region, offering cuisine from around the world in dozens of top-rated establishments. "The Waterfront at Port Chester" retail center has brought a multiplex movie theater to the Byram River shore, Costco Shoppers Warehouse, Bed, Bath & Beyond, Super Stop & Shop, Marshall's and several other stores. Port Chester's prodigious industrial growth during the first half of the 20th Century attracted large numbers of European immigrants, primarily from Italy, Germany, Poland and Ireland. Similarly, newcomers from Central and South America and the Caribbean have helped to fuel the village's recent revival. Latino-owned stores and restaurants have helped bring customers of all ethnic groups back to Main Street and Westchester Avenue.
The Port Chester Union Free School District are proud winners of two National Blue Ribbon School Awards; Port Chester Middle school honored in 2005 and John F. Kennedy Magnet School honored in 2010. Over 90% of the students in the Port Chester District are college bound after graduation. The district has SMARTboards and computers in every classroom, and the middle school and high school has state of the art science labs. Port Chester Union Free School District has partnerships with area corporations and universities that bring innovative programs to the classrooms and professional development to their teachers. Parents and community members play a pivotal role in supporting the schools, and all together contribute to the success of Port Chester students.