Oakland is a town in and the county seat of Garrett County, Maryland, United States. The population was 1,851 at the 2020 census. It is situ…Oakland is a town in and the county seat of Garrett County, Maryland, United States. The population was 1,851 at the 2020 census. It is situated only miles from the source of the Potomac River, which flows directly into Chesapeake Bay. It is also near the Wisp Resort at Deep Creek Lake. Oakland is part of the Pittsburgh media market.