Founded in 1893 by Charles Douglass (Frederick Douglas son) and his wife Laura, Highland Beach became the first African American town in Maryland. Charles and Laura bought 40 acres of beachfront land from another Black farmer, Daniel Brashers, who originally owned 48 acres of land. Charles wanted to use the land to build a summer house for himself, and a retirement home for his father. The two houses he built became known as “Twin Oaks” located in Annapolis, MD. After a few years, many other African Americans became aware of Highland Beach and decided to build houses there too. Soon it became a popular hangout in the summer for educated black people.

Highland Beach founder Major Charles R. Douglass (1844–1921), the youngest son of Frederick Douglass.

Photo Credit: Highland Beach Historical Collection

In the early 1900’s a hotel was built inside Highland Beach to accommodate the high number of guests it was bringing in. The hotel was a popular spot because there would be dances and church groups held every Saturday night and Sunday morning. The hotel turned into a private home around 1970 due to its popularity. They also had built summer houses for themselves located on the beach along with a tennis court built and families would host and place bets on tournaments.  

As the town was created 1893, it did not legally become incorporated until 1922, becoming the first African American summer resort in the country. Charles and Laura Douglass's son, Haley George, was a part of the delegation that got the town incorporated and soon after, he was elected as the first mayor of Highland Beach. By the 1950’s there were around 40 houses and only five year-round residents. 

Currently, there are a little over sixty houses in Highland Beach with most of them being owned by the descendants of the original settlers. The town is not all African American anymore as thirty percent of the residents are white. Over time some of the Black owners lost their homes due to the inability to pay the house rent, which opened room for other residences. While Highland Beach is an interesting place to travel to, there are no pets allowed nor is picnicking allowed. The mayor of the town is William H. Sanders III where he has been serving his 5th term since 2003.

Photo Credit: Christopher Busta-Peck