Oakland is a town in Garrett County, Maryland, United States, and its county seat. The population was 1,851 at the 2020 census. It is near …Oakland is a town in Garrett County, Maryland, United States, and its county seat. The population was 1,851 at the 2020 census. It is near Deep Creek Lake and the Wisp Ski Resort. Oakland was formally incorporated as a town in 1862.