Highland Beach MarylandATTRACTIONS & THINGS TO DO
Listed below are the best attractions and things to do near Highland Beach, Maryland.
1. Frederick Douglass Museum and Cultural Center (Twin Oaks)
HISTORIC HOME & MUSEUM
The Frederick Douglass Museum and Cultural Center, housed in the historic Twin Oaks cottage, preserves the legacy of Frederick Douglass and his family in Highland Beach. The cottage was built in 1895 for Douglass himself and contains artifacts and exhibits highlighting the African American community's history and achievements. Visitors gain insight into the town's founding and its role as a refuge during segregation.
2. Historic Highland Beach Walking Tour
GUIDED HERITAGE EXPERIENCE
The Historic Highland Beach Walking Tour offers a unique opportunity to explore the first African-American municipality in Maryland. Guests can stroll through leafy streets with homes named after influential Black leaders and learn about the town's significant history. The tour highlights the legacy and community spirit that continue to define Highland Beach.
3. Streets of Highland Beach
LEGACY-FILLED NEIGHBORHOOD
The streets of Highland Beach are named after prominent African American figures, reflecting the town's deep historical roots. Walking through the neighborhood provides a sense of its past, with landmarks commemorating guests like Harriet Tubman and W.E.B. Du Bois. The tranquil, tree-lined avenues create a living history lesson for visitors.
4. Chesapeake Bay Views
SCENIC WATERFRONT VISTAS
Highland Beach offers beautiful views of the Chesapeake Bay from various vantage points within the community. These waterfront panoramas provide a peaceful backdrop and have made the area a coveted retreat for generations. Visitors can enjoy leisurely strolls along the shoreline while soaking in the scenery.
5. Maryland State House
HISTORIC CAPITOL BUILDING
The Maryland State House, located in nearby Annapolis, is the oldest state capitol in continuous legislative use, dating back to 1772. It once served as the nation's capitol and features the largest wooden dome constructed without nails in the U.S. This National Historic Landmark is a must-see for history enthusiasts.
6. Docks at Annapolis
LIVELY HARBOR SCENE
The Docks at Annapolis are a bustling hub where historic buildings meet the waters of Chesapeake Bay. Boaters, locals, and tourists enjoy the vibrant atmosphere, with plenty of opportunities for waterfront dining and people-watching. The harbor is a focal point for events and scenic strolls.
7. United States Naval Academy
MILITARY EDUCATION ICON
The U.S. Naval Academy, established in 1845, is a prestigious institution training future Navy and Marine Corps officers. Its picturesque campus is open for guided tours, showcasing historic architecture and traditions. The Academy Museum and stunning chapel are visitor highlights.
8. Main Street Annapolis
SHOPPING AND DINING DISTRICT
Main Street Annapolis is renowned for its eclectic mix of boutiques, art galleries, and local eateries. The vibrant thoroughfare draws visitors for both its shopping options and its historic charm. Sidewalk cafes and unique shops make it a favorite destination for day-trippers.
9. Ego Alley
POPULAR WATERFRONT PROMENADE
Ego Alley is a narrow waterway downtown where boaters parade their vessels and visitors watch from nearby restaurants and walkways. The lively spot is famous for people-watching and its festive atmosphere. It's a quintessential Annapolis experience for those wanting a taste of local boating culture.
10. Chick & Ruth's Delly
ICONIC LOCAL EATERY
Chick & Ruth's Delly is a beloved Annapolis dining institution known for its hearty breakfasts, crab cakes, and quirky charm. The walls are lined with memorabilia, creating a nostalgic atmosphere for locals and visitors. Its pledge of allegiance ceremony and classic menu have made it a local legend.
11. Annapolis Maritime Museum & Park
BAY HISTORY AND ECOLOGY
The Annapolis Maritime Museum & Park immerses guests in the history, ecology, and tradition of Chesapeake Bay. Exhibits focus on the region's maritime heritage, oyster industry, and environmental stewardship. The waterfront setting offers interactive experiences for all ages.
12. Rams Head Tavern
MUSIC VENUE & PUB
Rams Head Tavern is a cornerstone of Annapolis nightlife, offering live music, craft beers, and a cozy historic ambiance. The venue features a diverse calendar of concerts ranging from local acts to touring musicians. Its menu blends classic pub fare with inventive twists.
13. Chart House
UPSCALE WATERFRONT DINING
Chart House is an upscale seafood restaurant perched at the water's edge, offering panoramic views of Spa Creek and the harbor. Diners enjoy fresh catches and classic steakhouse fare in a refined, nautical-themed setting. The restaurant is especially popular for special occasions and sunset dinners.
14. St. Anne's Church
HISTORIC COLONIAL PARISH
St. Anne's Church, founded in 1692, stands as one of Annapolis's oldest religious landmarks. The church's striking architecture and storied cemetery attract visitors interested in the city's colonial past. Guided tours reveal its deep connections to Maryland's early history.
15. Quiet Waters Park
RECREATION AND NATURE RETREAT
Quiet Waters Park is a sprawling oasis offering trails, gardens, playgrounds, and water access for kayaking or picnicking. The park's art gallery and seasonal ice rink add to its range of family-friendly activities. Visitors appreciate its peaceful setting just minutes from downtown Annapolis.