Highland Beach (historic core)
The original Douglass-founded enclave along Bay Highlands Drive, with Twin Oaks and century-old summer cottages on the Chesapeake.
Best time
Summer (June–September) for warm Chesapeake weather and peak Annapolis waterfront season.
Currency
USD
Language
English
Mid-range / day
USD 270
Is Highland Beach safe for Black travelers?
Highland Beach scores 4.6/5 (Excellent) on the ROAM BLK safety index for Black travelers. A quiet, historically Black residential enclave beside well-touristed Annapolis; welcoming, with the one caveat that Highland Beach itself is private property where residents’ privacy is expected.
Black Travel Profile
- Community welcome: 4.8/5
- Police climate: neutral
- Discrimination risk: low
- Black-owned business presence: moderate
Insider note: This is a heritage-pilgrimage stop, not a public-beach day trip — the town is private and its one attraction, the Frederick Douglass Museum at Twin Oaks, has been closed for renovation (virtual tours only), so check fdmcc.org and call ahead. Base in Annapolis (~10 min) for lodging, dining, and the surrounding Black-heritage sites.
Neighborhoods to Know
Venice Beach (adjacent)
The neighboring Black beach community that developed alongside Highland Beach and shares its founding history.
Downtown / City Dock, Annapolis
The nearby colonial capital's waterfront — home to the Kunta Kinte–Alex Haley Memorial, the Banneker-Douglass Museum, lodging and dining.
Must-Visit Places
Frederick Douglass Museum & Cultural Center (Twin Oaks) Black-Owned
The 1890s summer house built for Frederick Douglass, now a museum on his family and Highland Beach's founding (call ahead — reopening after renovation).
3200 Wayman Ave, Highland Beach, Maryland
Highland Beach waterfront & town Black-Owned
The historic Chesapeake Bay enclave itself — the founding shoreline and cottages of America's first Black resort town (private; view respectfully).
Highland Beach, Maryland
Banneker-Douglass Museum (Annapolis)
Maryland's official state museum of African American heritage, with the permanent 'Deep Roots, Rising Waters' exhibit.
84 Franklin St, Annapolis, Maryland
Kunta Kinte–Alex Haley Memorial (City Dock)
The only U.S. memorial marking the name and arrival point of a named enslaved African, from Haley's 'Roots.'
City Dock, Annapolis, Maryland
Annapolis City Dock & historic waterfront
The walkable colonial harbor district for dining and boat access — the practical base for Highland Beach visitors.
City Dock, Annapolis, Maryland
Visa
No visa required for US citizens (domestic).
Frequently asked questions
Is Highland Beach safe for Black travelers?
Highland Beach scores 4.6 out of 5 (Excellent) on the ROAM BLK safety index for Black travelers. A quiet, historically Black residential enclave beside well-touristed Annapolis; welcoming, with the one caveat that Highland Beach itself is private property where residents’ privacy is expected.
Which neighborhoods in Highland Beach are good for Black travelers?
Highland Beach (historic core), Venice Beach (adjacent), Downtown / City Dock, Annapolis. The original Douglass-founded enclave along Bay Highlands Drive, with Twin Oaks and century-old summer cottages on the Chesapeake.
Are there Black-owned businesses in Highland Beach?
Black-owned spots ROAM BLK recommends include Frederick Douglass Museum & Cultural Center (Twin Oaks), Highland Beach waterfront & town.
When is the best time to visit Highland Beach?
Summer (June–September) for warm Chesapeake weather and peak Annapolis waterfront season.
How much does a day in Highland Beach cost?
Budget: USD 140 · Mid-range: USD 270 · Luxury: USD 500 per day, per ROAM BLK estimates.
Plan your Highland Beach trip in ROAM
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