Chester is a town in Middlesex County, Connecticut, United States. The population was 3,743 at the 2000 census. The town center is also defined by the U.S. Census Bureau as a census-designated place (CDP).

The Wangunks, a river tribe of Native Americans, occupied the land called Pattaconk prior to English settlement of the area in 1692. The town was formed from the northern quarter of Saybrook and incorporated in 1836. Back in 1769, Jonathan Warner was granted permission to operate a ferry across the Connecticut River that became the Chester-Hadlyme Ferry, the second-oldest continuously operating ferry service in Connecticut. Its location is currently a state historical landmark.

According to the United States Census Bureau, the town has a total area of 16.8 square miles (44 km²), of which, 16.0 square miles (41 km²) of it is land and 0.8 square miles (2.1 km²) of it (4.75%) is water. The CDP has a total area of 2.1 square miles (5.4 km²) of which 1.46% is water.

As of the census of 2000, there were 3,743 people, 1,510 households, and 1,005 families residing in the town. The population density was 233.5 people per square mile (90.2/km²). There were 1,613 housing units at an average density of 100.6 per square mile (38.9/km²). The racial makeup of the town was 96.79% White, 0.85% African American, 0.35% Native American, 0.83% Asian, 0.05% Pacific Islander, 0.24% from other races, and 0.88% from two or more races. Hispanic or Latino of any race were 1.71% of the population.

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