Highland Beach: A Historic Chesapeake Bay Community

Charles and Laura Douglass established Highland Beach at a time when Black Americans faced exclusion from many seaside resorts. The community became a place where families could own property and spend summers by the Chesapeake Bay. Its history is connected to the wider story of Black leisure, homeownership, and community-building around the turn of the 20th century. That past is still visible in the town’s identity rather than confined to a single monument. Highland Beach remains a small, lived-in place, with generations of family connections alongside newer residents. Twin Oaks, a house built for Frederick Douglass, is its best-known historic site. He died before he could live there; today the property is associated with the Frederick Douglass Museum and Cultural Center.

The town sits on a narrow stretch of land beside the bay, near the mouth of the South River. Water, mature trees, and closely spaced houses give it a different feel from the busier parts of the Annapolis area. The shoreline and views are central to Highland Beach’s character, but much of the beach and waterfront access belongs to residents and property owners. This is not a place with a boardwalk, a row of seafood restaurants, or a public swimming beach. A short visit is more likely to focus on its history and setting than on a full day of activities. The coastal location also means weather matters: summer can be hot and humid, while storms and high water can affect low-lying areas.

Highland Beach is close enough to Annapolis to fit into a wider visit to Maryland’s Chesapeake Bay shore. A car is the practical way to reach it, and dining, lodging, and most other services are found outside the town. Its small size makes the contrast clear: this is an established residential community, not a resort set up for casual sightseeing. Anyone hoping to see Twin Oaks should check current tour arrangements before going. For a broader view of the nearby waterfront, Thomas Point Park lies farther along the peninsula, with the offshore Thomas Point Shoal Lighthouse in the surrounding bay. These places add context without changing the main reason Highland Beach stands out: its unusually strong connection between a specific shoreline and generations of Black family and civic history.