Leonardtown High School is a comprehensive public high school of 1,920 students in grades 9-12. It offers college preparatory programs and programs that prepare students for business and technical occupations.

Students select a program from one of five career clusters that provides a focus and structure designed to prepare students for post-secondary work and study. Specific college preparatory programs may include CM level, Honors level, and Advanced Placement level classes. Standard level classes are designed for students preparing to work or attend a trade school or community college.