Highland Beach, MD

Set right on the Chesapeake Bay just south of Annapolis, Highland Beach is a quiet waterfront enclave with deep historic roots. The town was founded in 1893 by Major Charles Douglass, son of abolitionist Frederick Douglass, and his wife Laura as a seaside retreat for family and friends. While Frederick Douglass passed away before his own summer cottage here was finished, the Douglass family legacy helped shape the community from its earliest days on the water.

ATTRFamartin / CC BY-SA 4.0

In 1922, Highland Beach became the first incorporated Black municipality in Maryland, regularly hosting cultural figures like Langston Hughes, Booker T. Washington, and W.E.B. Du Bois. Today, it is a tight-knit community of around eighty homes, shared by seasonal cottagers and year-round neighbors. Many properties are still cared for by descendants of the original founders, giving this peaceful bayside neighborhood a rich sense of tradition and easygoing coastal charm.