Introduction: A Place Like No Other
Nestled along the shimmering shorelines at the tip of the Annapolis Neck peninsula, Highland Beach is a neighborhood whose story is as inspiring as its sunsets. With roots that reach back into the late 19th century, this close-knit community is much more than a picturesque waterfront destination. Highland Beach is a living tribute to African American achievement, self-determination, and enduring pride. For generations, the clapboard cottages and leafy streets here have echoed the laughter of summer families, the wisdom of elders, and the ongoing efforts to preserve a uniquely hopeful legacy.
Origins: The Vision of Freedom’s Children
Highland Beach’s origins are steeped in vision and hope. The neighborhood was founded in 1893 by Charles Douglass, the son of famed abolitionist Frederick Douglass, and his wife Laura Douglass. At a time when segregation barred Black families from enjoying resort amenities elsewhere along the Chesapeake, Charles and Laura Douglass purchased a 40-acre tract—today roughly bounded by Douglass Avenue, Spring Avenue, and Bay Avenue. Their aim was to create a haven where African Americans could enjoy recreation, fellowship, and the Chesapeake’s beauty without fear of discrimination.
The name "Highland Beach" comes quite simply from the high land overlooking the beach and the sparkling Chesapeake Bay—a place apart, meant to inspire both respite and pride.
Early Days: Summer Retreats and Social Hubs
In those earliest years, Highland Beach’s sandy lanes and shaded plots quickly became a magnet for accomplished African American families throughout the Mid-Atlantic. Notable summer residents included poets, educators, judges, and physicians—folks like W.E.B. Du Bois and Paul Laurence Dunbar, who built one of the first homes on Douglass Avenue. With their welcoming porches and open windows, these cottages—many of which still stand—formed the heart of a vibrant seasonal community.
Social life revolved around gatherings and simple pleasures:
- Picnics and crab feasts beneath the shade trees of Douglass Avenue.
- Dances and card games at private homes.
- Children running down Bay Avenue to the water or biking along Walnut Drive.
Highland Beach became known up and down the coast as a place of relaxation, but also of intellectual kinship and renewal.
Key Milestones: Growth, Recognition, and Incorporation
From its original forty acres, Highland Beach expanded over the decades as land was subdivided and more families built summer homes. Each generation contributed to the growing fabric of the community, establishing traditions and advocating for civic improvements.
A few key milestones mark Highland Beach’s evolution:
- 1922: The Highland Beach Protective Association was formed to ensure the neighborhood’s well-being and to address infrastructure needs like street maintenance and mosquito control.
- 1926: The community was incorporated as a town—the first African American incorporated municipality in Maryland. This gave Highland Beach an unprecedented degree of self-governance, with an elected mayor and commissioners.
- Post-WWII: The neighborhood welcomed both year-round and summer residents, adapting to changing times while holding fast to its founding spirit.
- 1970s-Present: Longtime families have joined with newcomers to preserve the area’s historic architecture and fighting to keep Highland Beach’s unique heritage alive.
Landmarks and Notable Sites: Echoes of the Past
Walking through Highland Beach today, you’ll find reminders of its rich history at almost every turn.
- Frederick Douglass Museum and Cultural Center: Perhaps the neighborhood’s most renowned landmark, the center is housed in the original home built by Charles Douglass for his father, Frederick Douglass, who sadly passed away before he could summer there. The charming, white house stands proudly near the intersection of Douglass Avenue and Bay Avenue—now welcoming visitors as a museum and community gathering place.
- Paul Laurence Dunbar House: On Douglass Avenue, you can still spot the cottage built by the famous poet. It’s now a private residence, but its distinctive lines recall the creative energy that Highland Beach attracted.
- Douglass Park: A beloved green space with views over the water, this is where families gather for community picnics, children play, and neighbors greet each other on summer strolls.
- The historic cottages: Many homes throughout Highland Beach, like those lining Walnut Drive and Beach Drive, exhibit the original shingle and woodwork styles of the early-20th century, standing as testament to the careful stewardship of residents over the years.
Evolving Community: Past and Present
While summer remains a magical time in Highland Beach—with its Fourth of July parades, kayaking in Oyster Creek, or quiet mornings along Bay Avenue—the neighborhood is now home to an increasing number of year-round residents. Recent years have seen a dedicated wave of historic preservation, as well as an influx of young families committed to honoring the past while building for the future.
Today, Highland Beach maintains its spirit through:
- The efforts of the Highland Beach Town Hall—located on Bay Avenue—which serves as an anchor for community events.
- Ongoing restoration projects, such as those led by the Highland Beach Historical Society.
- Active engagement with civic issues, environmental stewardship, and educational programming through partnerships with Annapolis Neck institutions.
Neighbors continue to celebrate together at Douglass Park, keep up the gardens along Douglas Avenue, and collaborate to ensure both the physical and cultural landscape remains vibrant.
Conclusion: The Heartbeat of Heritage
To walk or bike through Highland Beach is to feel the heartbeat of heritage—a call to remember, to appreciate, and to continue building on the remarkable vision of its founders. More than its sandy beaches or charming homes, what truly makes Highland Beach special is an enduring sense of unity and pride. Here, in the sunlit shimmer of the Chesapeake Bay, the legacy of freedom and community continues to grow—just as it has for more than 130 years.