Annapolis Neck

Highland Beach, Annapolis Neck Neighborhood

Highland Beach offers a peaceful and calm environment with predominantly single detached homes and townhouses built around 1982. The neighborhood features spacious residences, often with three or more bedrooms, providing comfortable living options. Residents have access to several restaurants, enhancing local dining opportunities. Elementary-level private and public schools serve the area, adding to community resources. While green spaces are not abundant within the neighborhood itself, nearby parks offer attractive options for outdoor enjoyment. The streets maintain a quiet atmosphere, contributing to a serene setting. Convenient parking and easy car access support travel throughout the surrounding community.

People who prefer a calm environment will enjoy Highland Beach. Most areas in Highland Beach are especially quiet, as noise from streets and other parts of the city is rarely an issue. Parks aren't well-situated, making it occasionally hard to access them. Despite that, residents will be able to access green spaces in nearby neighborhoods.

Highlights of Highland Beach

Parks, schools, dining, and what makes this neighborhood special

🌊 Highland Beach Community Beach

This private, resident-only stretch of beach along the Chesapeake Bay offers stunning waterfront views and a peaceful atmosphere, making it the heart of leisure and social life in this historic African American-founded community.

🏘️ Heritage Walking Trail

Winding through the neighborhood, this trail features interpretive signage about Highland Beach's rich history—notably its founding in 1893 as a summer retreat for Black families and intellectuals, including Frederick Douglass’s descendants.

🏠 Twin Oaks: Frederick Douglass Summer House

The original summer home of Charles Douglass, son of Frederick Douglass, ‘Twin Oaks’ is a National Historic Landmark and an enduring symbol of Highland Beach’s origins and cultural significance.

🌳 Douglass Memorial Park

Located at the center of the neighborhood, this small green space serves as a communal gathering point and hosts local events, with a playground and benches inviting peaceful relaxation under shade trees.

🚪 Highland Beach Town Hall

Serving as the civic heart of the community, the Town Hall on Bay Avenue is where council meetings and community activities take place, reflecting the self-governance and active, close-knit spirit of Highland Beach.

Highland Beach

This July in Highland Beach

Things to do, events, and what's happening this month

July 5, 2026

The Red Barn Sessions: Cory Seznec / Rhys Jones

Hollywood Farm, The Red Barn (625 Holly Drive, Broadneck Peninsula) • 6:00 PM–10:00 PM

An intimate acoustic concert at nearby Hollywood Farm offers Highland Beach residents a scenic and cozy evening under the stars, perfect for enjoying local music and community gathering just a short drive away.

July 7, 14, 21, & 28, 2026

Chronic Sailing’s ‘Tunesday’ Floating Concert Series

Back Creek / Ellen O. Moyer Nature Park, Annapolis • 90 minutes beginning ~90 minutes before sunset

This free weekly floating concert series allows locals to enjoy live music from the water or park shore—ideal for Highland Beach families looking for a unique waterfront summer outing.

July 9, 16, 23 & 30, 2026

Tides & Tunes Concert Series

Annapolis Maritime Museum & Park (723 Second Street, Annapolis) • 7:00 PM–9:00 PM

Free weekly waterfront concerts at the Maritime Museum give Highland Beach residents engaging family-friendly summer evenings immersed in maritime heritage and live music.

July 11, 2026

The Travelin' McCourys Concert

Rams Head On Stage, Annapolis • 8:00 PM

Catch an energetic bluegrass show just down the road at Rams Head On Stage—a great option for music lovers in Highland Beach seeking a note‑perfect night out close to home.

July 16, 2026

Royale Lynn w/ Stone Horses

Rams Head On Stage, Annapolis • 8:00 PM

An evening concert featuring lively Americana music at Rams Head On Stage—easy for locals to get to and ideal for a fun night out amidst a vibrant music scene.

July 28, 2026

Bilal Concert

Rams Head On Stage, Annapolis • 8:00 PM

A soulful performance by Bilal at Rams Head On Stage offers Highland Beach residents a chance to enjoy acclaimed R&B music within a short drive and vibrant venue.

From the Neighborhood

Stories, updates, and things to know in Highland Beach

Know Your Neighborhood

Local characteristics and demographics for Highland Beach

Neighborhood Characteristics

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Demographics

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