The Chester School District is a fully accredited elementary district responsible for the education of students in Kindergarten through eighth grades. Students in grades nine through twelve go to the West Morris Regional High School District.The district is composed of Dickerson Elementary School (K-2), Bragg Intermediate School (3-5), and Black River Middle School (6-8). Dickerson and Bragg Schools are located on Route 24, east of Chester Borough; Black River Middle School is on Route 513 (North Road), north of Chester Borough. The school district serves two municipalities, Chester Borough and Chester Township. The Borough of Chester is a 1.6 square mile village centered on a main street lined with specialty shops, old homes, and historic buildings. Widely known for its distinctive charm, Chester Borough draws many visitors who enjoy a day in the country atmosphere.The surrounding Chester Township is a 29.3 square mile residential community made up of farms, estates, and attractive housing developments. 

The two municipalities share other common bonds in addition to the school system. These include the public library, an active athletic association, a theater in the round, and many civic organizations. Residents also have ready access to nearby colleges, hospitals, shopping centers, and cultural facilities located in Morris County and nearby Somerset and Sussex Counties.