Shady Side is a census-designated place (CDP) in Anne Arundel County, Maryland, United States. The population was 5,803 at the 2010 census. According to the United States Census Bureau, the CDP has a total area of 8.0 square miles (20.7 km2), of which 6.8 square miles (17.5 km2) is land and 1.2 square miles (3.2 km2), or 15.57%, is water.
In the 1790s the area was known as the Great Swamp.Capt. Salem Avery House was listed on the National Register of Historic Places in 2005. The Lula G. Scott Community Center was listed n 2009. Shady side was once served by the sidewheel passenger steamer Emma Giles that operated from Baltimore, Maryland, making up to five trips per week.