Chester is a town in Orange County, New York, United States. The population was 11,981 at the 2010 census. Chester contains a village, also called Chester. According to the United States Census Bureau, the town has a total area of 25.2 square miles (65.4 km²), of which, 25.2 square miles (65.2 km2) of it is land and 0.1 square miles (0.2 km2) of it (0.24%) is water.
The town was first settled in the 1700s by Europeans.The economy of the early town was based on dairy products, particularly milk, which was brought on by the completion of the Erie Railroad, which ran through Chester, in 1841. After its completion, local farmer Phil Gregory would ship 240 quarts of milk to New York City, which earned the railroad $1.20 in freight charges; Gregory's business eventually grew to 300,000 quarts of milk a day, which in turn gave the Erie Railroad over $1000 in profit.