Leonardtown is a town in and the county seat of St. Mary's County, Maryland, United States. The population was 2,930 at the 2010 census. Leonardtown is perhaps most famous for the national oyster-shucking championship that is held annually at the St. Mary's County fairgrounds. Historic Leonardtown includes both a large public high school and a public middle school Leonardtown Middle School as well as a Catholic high school and an elementary school Leonardtown Elementary School, offices of the county government, and St. Mary's Hospital which serves the healthcare needs of the county. The College of Southern Maryland maintains a growing satellite campus within city limits, including an aquatic center. An upscale home development located in the Breton Bay area is just outside town, notable for both its country club golf course and swimming pool. Leonardtown's population has grown significantly since 1990 as a result of the town's proximity to Patuxent River Naval Air Station and the Washington metro area.

Upper Marlboro, officially the Town of Upper Marlboro, is the seat of Prince George's County, Maryland, United States. The population within the town limits was 631 at the 2010 U.S. Census, although Greater Upper Marlboro is many times larger.

St. Mary's County, established in 1637, is a county located in the U.S. state of Maryland. As of the 2010 census, the population was 105,151. Its county seat is Leonardtown. The name is in honor of Mary, the mother of Jesus.St. Mary's County comprises the California-Lexington Park, Maryland Metropolitan Statistical Area, which also is included in the Washington-Baltimore-Arlington, DC-MD-VA-WV-PA Combined Statistical Area. It is part of the Southern Maryland region. The county was the home to the first Maryland Colony, and the first capitol of the Colony of Maryland. Settled by English Catholics, it is considered to be the birthplace of religious freedom in North America, at a time when the British colonies were settled primarily by Protestants.The county is home to the Patuxent River Naval Air Station and St. Mary's College of Maryland. Traditionally, St. Mary's County has been known for its unique and historic culture of Chesapeake Bay tidewater farming, fishing, and crabbing communities. But with the advent of the military bases, growth of an extensive defense contractor presence, and the growth of St. Mary's College of Maryland, as well as increasing numbers of long-distance Washington, D.C. commuters, it has been undergoing a decades-long transformation which has seen the county's population double since 1970.

Talbot County is located in the heart of the Eastern Shore of Maryland in the U.S. state of Maryland. As of the 2010 census, the population was 37,782. Its county seat is Easton. The county was named for Lady Grace Talbot, the wife of Sir Robert Talbot, an Anglo-Irish statesman, and the sister of Lord Baltimore.Talbot County comprises the Easton, MD Micropolitan Statistical Area, which is also included in the Washington–Baltimore–Arlington, DC–MD–VA–WV–PA Combined Statistical Area. Talbot County is bordered by Queen Anne's County to the north, Caroline County to the east, Dorchester County to the south, and the Chesapeake Bay to the west.