Windy Hill Middle School offers a range of academic and extracurricular options to students. Its syllabus includes English, mathematics, science, special education, social studies, language arts and music. The school conducts classes in foreign languages and physical education. It maintains a library and media center that features a collection of books and reference and instructional materials. The school also administers the English for Speakers of Other Languages program. It organizes school plays and math count events, as well as operates various after-school clubs. The school offers several sports programs, including basketball, soccer and cheerleading. Windy Hill Middle School operates a parent-teacher-student association that conducts fundraising events and programs. It is a part of Calvert County Public Schools, which governs various educational institutions.