Many of the families are employed by NAS Patuxent River, government contractors, St. Mary's College of Maryland, St Mary's County government and others involved in the traditional agriculture and water related businesses.

6 seeded Leonardtown Raiders Varsity Baseball Team defeated the No.

1 seeded Walt Whitman Vikings 2-0 at Regency Furniture Stadium to claim the MPSSAA Class 4A Baseball State Championship.

On May 25, 2024 the Leonardtown softball team won the MPSSAA Class 4A Softball State Championship, beating Eleanor Roosevelt High School by a score of 14-0 at the University of Maryland.

Kanagawa Prefectural Hibarigaoka High School in Japan became the sister school of Leonardtown High in October 1991, when the county board of education and representatives from Maryland formalized an agreement.