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.

Garrett County is the westernmost county of the U.S. state of Maryland completely within the Appalachian Mountains. As of the 2020 census, the population was 28,806, making it the third-least populous county in Maryland. Its county seat is Oakland. The county was named for John Work Garrett (1820–1884), president of the Baltimore and Ohio Railroad. Created from Allegany County in 1872, it was the last county to be formed in the state.