Dorchester County Public Schools The Dorchester County Board of Education seeks an outstanding educational leader to serve as the Superintendent of Schools beginning on July 1, 2024. Dorchester County, Maryland, with a population of 29,300, is the Eastern Shore’s largest county with 593 square miles of land and 108 square miles of water. While the county is home to more than 750 businesses, it is also rich in recreational facilities and natural resources. The Dorchester County PublicSchool system provides the educational foundation for the county’s children. Information about the 5000-student Dorchester County Public Schools: There are 12 schools: two high schools, a career and