June 30, 2026 · The BlackEvents Team

Highland Beach, Maryland: Frederick Douglass's Chesapeake Legacy (Founded 1893)

Founded in 1893 by Charles Remond Douglass — Frederick Douglass's son — after being denied service at a nearby resort. Twin Oaks. The oldest incorporated Black municipality in Maryland. Here is the Highland Beach guide.

Highland Beach, Maryland was founded in 1893 by Charles Remond Douglass — Frederick Douglass's son — after Charles was denied service at Bay Ridge, a nearby whites-only Chesapeake resort. Charles purchased 44 acres of Chesapeake Bay waterfront property and founded what would become the oldest African American-founded incorporated municipality in Maryland.

He built Twin Oaks — a summer cottage — for his father, Frederick, in 1895. Frederick died before he could vacation there, but Twin Oaks remains standing today as the Frederick Douglass Museum and Cultural Center.

Here's the Highland Beach guide.

The essentials

Founded: 1893 Founder: Charles Remond Douglass (Frederick Douglass's son) Location: Anne Arundel County, Maryland, on the Chesapeake Bay Nearest city: Annapolis, MD (adjacent) Historic significance: Oldest African American-founded incorporated municipality in Maryland Twin Oaks (Frederick Douglass Museum): built 1895 as Frederick Douglass's summer cottage; now the Frederick Douglass Museum and Cultural Center

Who founded Highland Beach

Charles Remond Douglass (1844-1920) was Frederick Douglass's son. A veteran (he served in the 54th Massachusetts, the Union's most famous Black regiment), a federal employee, and a businessman, Charles carried his father's civil rights legacy forward through his own work.

The founding incident: In the early 1890s, Charles and his wife were denied service at Bay Ridge, a whites-only resort on the Chesapeake Bay near Annapolis. Rather than accept the humiliation, Charles decided to solve the underlying problem: he would create a Black-owned resort community.

In 1893, Charles purchased 44 acres of Chesapeake waterfront property just south of Bay Ridge. He subdivided the land, sold lots to Black families, and founded what he called Highland Beach.

In 1895, Charles built Twin Oaks — a Victorian-style summer cottage — for his father Frederick. Frederick died on February 20, 1895, before he could summer at Twin Oaks. But the cottage remained in the Douglass family.

In 1922, Highland Beach was incorporated as a municipality — making it the oldest African American-founded incorporated municipality in the state of Maryland.

The mid-century community

Through the 20th century, Highland Beach became one of the most important Black summer communities on the Eastern Seaboard — smaller and quieter than Oak Bluffs or American Beach, but with a dense Black professional and political class.

Regular residents and visitors included:

Members of the Douglass family across generations
Federal government officials and Black political leaders from DC (an easy drive to Highland Beach)
Members of the Black professional class from Baltimore, DC, and Philadelphia
Various educators, physicians, attorneys, and business owners

The community remained relatively small — a few hundred homes — which allowed it to preserve its character in a way that larger Black beach communities sometimes couldn't.

Twin Oaks — the Frederick Douglass Museum & Cultural Center

Twin Oaks — Charles Douglass's summer cottage built for his father Frederick in 1895 — is now the Frederick Douglass Museum and Cultural Center (FDMCC).

The Museum:

Deepens public understanding of Frederick Douglass's life and his family
Preserves the social and cultural histories of Highland Beach and Venice Beach
Provides access to these resources for education and research
Offers docent-led tours by trained interpreters
Curates exhibits highlighting the community's history

Website: fdmcc.org

Location: Highland Beach, MD

Visiting: By appointment or during scheduled programming; check the FDMCC or town of Highland Beach website for current hours.

Venice Beach

Venice Beach is Highland Beach's neighboring subdivision — also historically Black-owned, also part of the broader Highland Beach community.

The FDMCC preserves the history of both Highland Beach and Venice Beach as connected communities.

The 2026 programming

Specific 2026 event dates at Frederick Douglass Museum and Cultural Center should be verified directly with the museum. Typical programming includes:

Guided tours of Twin Oaks and the community
Lectures and educational programming
Special exhibitions
Community events tied to Frederick Douglass's birthday (February 14) and other Douglass-related anniversaries
Summer programming during peak visitor season

Contact the Frederick Douglass Museum and Cultural Center at fdmcc.org for current 2026 programming, tour availability, and special events.

What Highland Beach looks like today

Highland Beach in 2026 is:

A small, quiet residential town on the Chesapeake Bay
The oldest African American-founded incorporated municipality in Maryland
Home to the Frederick Douglass Museum and Cultural Center
A functioning residential community — not an open-air museum
Physically small — a few hundred residents

The town is deliberately quiet and residential. It doesn't have the tourism infrastructure of Oak Bluffs or the events calendar of Idlewild. What it has is deep historic significance and a community that continues to steward that significance.

What to see and do

In Highland Beach:

Twin Oaks / Frederick Douglass Museum — the essential visit
The community walk — historic homes, Chesapeake views
The town hall (in the historic building)
Bay views from the community's shoreline

Nearby:

Downtown Annapolis — 15 minutes drive, historic city, Naval Academy, restaurants
The Chesapeake Bay Bridge — impressive engineering, beautiful views
Sandy Point State Park — public beach access on the Chesapeake
Kunta Kinte-Alex Haley Memorial in downtown Annapolis — significant historic site
The Banneker-Douglass Museum in Annapolis — dedicated to Maryland's African American history

Getting there

Highland Beach is easily accessed by car:

From Washington, DC: ~45 minutes drive
From Baltimore: ~30 minutes drive
From Philadelphia: ~2 hours drive
From New York City: ~4 hours drive

Nearest airport: Baltimore/Washington International (BWI) — 30 minutes.

Public transit: limited direct options. A car is essentially required for a proper visit.

See getting to American Beach + Highland Beach → for the fuller logistics playbook.

Where to stay

Highland Beach itself has minimal lodging supply — this is a residential community.

Lodging options:

Annapolis (15 minutes) — full hotel supply, from budget chain to historic waterfront
Bay Ridge / Eastport / Annapolis waterfront — hotels, B&Bs, Airbnb
Airbnb in Highland Beach itself — very limited but real; check current listings
Kent Island (30 minutes) — resort-town supply

Where to eat

Highland Beach itself: minimal restaurant supply.

In Annapolis (15 minutes):

Vin 909 — waterfront, considered
Boatyard Bar & Grill — casual, waterfront
Preserve — dressed, downtown
Cantler's Riverside Inn — Maryland crab, classic
Various downtown Annapolis restaurants — full range

Consider driving to Baltimore for the fuller dining scene.

What to wear

Chesapeake Bay resort community, casual:

Sundresses, linen, khakis
Sandals
Hat
Layer for evening (bay breezes)
SPF

When to visit

Best months: April through October. Chesapeake weather is at its most pleasant.

Peak season: June-August. Warm, sometimes humid.

Shoulder: April-May and September-October. Excellent weather, fewer crowds.

Off-season: November-March. Cooler, quieter; Museum may have limited hours.

The etiquette

Highland Beach is a residential town. Behave accordingly:

Respect residential character — this is not an open-air museum
Book Museum visits in advance when possible
Ask before photographing homes or residents
Support the Museum — memberships, donations, ticket purchases
Learn the history before visiting — the community rewards prepared visitors
Combine your visit with the Banneker-Douglass Museum in Annapolis for the fuller historical context

What the community means

Highland Beach's founding was an act of civil rights self-help. When denied service, Charles Douglass didn't accept the exclusion or wait for legal remedy — he purchased land and built a community his family and community could actually use.

The community he founded has stood for 130+ years. That endurance is itself a form of continuing civil rights work: the preservation of Black-owned property, Black civic incorporation, and Black cultural memory.

Frederick Douglass never saw Twin Oaks completed. But the cottage his son built for him — and the town his son founded — remain as living monuments to what the Douglass family did, individually and collectively, for American civil rights.

Visiting Highland Beach is engagement with that continuity.

Combining Highland Beach and American Beach

If you're doing a "Historic Black Beaches" trip:

Highland Beach + American Beach can be combined as a DMV → Northeast Florida drive:

DMV (Highland Beach) → drive south
Charleston, SC — worthwhile stop
Savannah, GA — worthwhile stop
Amelia Island, FL (American Beach)

The drive is 12+ hours; make it a multi-day road trip.

Or fly to each independently:

BWI/DCA/IAD → Highland Beach — 45 minutes to Highland Beach
JAX → American Beach — 30 minutes to Amelia Island

1893. Charles Douglass. Twin Oaks. The oldest African American-founded incorporated municipality in Maryland. Still here.