Welcome to Chestertown Middle School. Located on the Chester River in Kent County on Maryland’s upper Eastern Shore, Chestertown Middle School is situated within the town limits of Chestertown. The original brick structure was built in 1946. It served as Chestertown High School until consolidation created Kent County High School in 1971. Chestertown Middle School was remodeled in 1975 and has served as a middle school since.

The town of Chestertown is one of five incorporated towns within the county. The town’s economy relies on farming, small business and industrial operations. Chestertown houses Washington College, a small liberal arts college, which provides our school with many volunteers and our high school students with college courses, and serves the community with many employment opportunities.

Chestertown Middle School is located at 402 East Campus Avenue in Chestertown, Maryland. A staff of forty-six full or part-time employees operates Chestertown Middle School. The staff is comprised of one (1) principal, one (1) assistant principal, six (6) instructional assistants, one (1) media instructional assistant, two (2) guidance counselors, four (4) special education teachers, one (1) part-time speech therapist, one (1) music teacher, one (1) art teacher, one (1) physical education teacher, one (1) computer technology teacher, one (1) half-time foreign language teacher, and seventeen (17) academic classroom teachers.

By adhering to our mission statement, “Chestertown Middle School will provide successful learning for all students through a quality educational program,” we will accomplish our ultimate goal – our students will be very well prepared for high school and their life beyond.