Douglass Summer House

Highland Beach is a town in Anne Arundel County, Maryland, United States. Per the 2020 census, the population was 118. The town was founded late in the 19th century by affluent African Americans from Washington, D.C. and Baltimore, looking for a summer retreat on the Chesapeake Bay. The town's incorporated status gave it a unique standing in empowering it to maintain its own police force. Celebrities with homes there have included historian and author Alex Haley, actor and comedian Bill Cosby, and tennis champion Arthur Ashe. Street names in the town include Crummell, Dunbar, Henson, Augusta, Douglass, Langston, and Washington, which were chosen to honor leading African Americans.

The Philip Merrill Environmental Center is a Green building owned and operated by the Chesapeake Bay Foundation. Built in 2001, the Merrill Center is located in Annapolis, Maryland on the western shore of the Chesapeake Bay. The building serves as the headquarters office building for the CBF, but is also available to rent for business and social occasions.The center is named for Philip Merrill, an American diplomat, publisher, banker, and philanthropist. The building was the first to receive the Leadership in Energy and Environmental Design (LEED) "Platinum" rating from the United States Green Building Council. This recognition confirmed that the center was the most environmentally friendly building in the country at the time when it was built. Items used in the building include recycled materials, renewable resources, and passive and active solar power and use.

Arundel-on-the-Bay (also referred to as "AOTB") is a former post village and resort area in Anne Arundel County, Maryland, United States, located approximately 2 miles (3.2 km) southeast of Annapolis. Arundel-on-the-Bay is located on a peninsula known as the Annapolis Neck and is a peninsula in and of itself, bordered on the east and south by the Chesapeake Bay, and by Fishing Creek on the west. Located near Highland Beach, Arundel-on-the-Bay was formerly an enclave of vacation residences and undeveloped property which attracted affluent African Americans when Jim Crow laws were in effect, when entrance to other resort areas was barred to non-whites. The community now holds approximately 345 homes. Arundel-on-the-Bay is a special tax district; each year a portion of property taxes are reserved by Anne Arundel County for improvements and maintenance of the shoreline. The community owns a private beach and pier, boat ramp, and boat launch for community use. The Thomas Point Lighthouse is visible and a short boat ride from the Arundel-on-the-Bay community beach. Notable residents include Aris T. Allen, Jr., son of Dr. Aris T. Allen, the first African American chair of the Maryland Republican Party and Kurt Schmoke, former and first African American mayor of Baltimore.

Carr's Beach, founded in 1926, was a beachfront resort on the Chesapeake Bay that catered to African American patrons during segregation.Located just south of Annapolis, Maryland, Carr's Beach was established as a recreational area during the Jim Crow-era when African-Americans were denied entry into 'Whites-only' establishments. Other nearby beachfront resorts used for this purpose included Sparrow’s Beach, Elktonia Beach, Bembe Beach, Highland Beach, Venice Beach, Oyster Harbor, and Arundel-on-the-Bay.Carr's Beach was a stop on the Chitlin' Circuit and hosted musical acts like Chuck Berry, Billie Holiday, Duke Ellington, and Ike & Tina Turner.The resort ceased operations in 1974.In August 2022, the City of Annapolis acquired Carr's Beach to preserve it as a park.

The Key School is an independent coeducational school, located in the neighborhood of Hillsmere Shores in Annapolis, Maryland. The Key School was established by a group of tutors from St. John's College in 1958. Key is a member of the National Association of Independent Schools (NAIS).

Sparrow's Beach was a beachfront resort on the Chesapeake Bay that catered to African American patrons during segregation in the American South.Located just south of Annapolis, Maryland, Sparrow's Beach was established as a recreational area during the Jim Crow-era when African-Americans were denied entry into 'Whites-only' establishments. Other nearby beachfront resorts used for this purpose included Carr's Beach, Elktonia Beach, Bembe Beach, Highland Beach, Venice Beach, Oyster Harbor, and Arundel-on-the-Bay.In August 2022, the City of Annapolis purchased what remains of Sparrow's Beach, Carr's Beach, and Elktonia Beach to preserve the land as a park.

Hillsmere Shores was a census-designated place (CDP) in Anne Arundel County, Maryland, United States. It is a suburb of Annapolis. The population was 2,977 at the 2000 census. It was included in the Annapolis Neck CDP at the 2010 census. Built in phases, beginning in 1960, the community has been home to The Key School, a non-sectarian private school, since the 1960s.

Annapolis Neck, a suburb of Annapolis, is a census-designated place in Anne Arundel County, Maryland, United States. As of the 2010 census, its population was 10,950.

The South River is a 10-mile-long (16 km) tributary of the Chesapeake Bay in Anne Arundel County, Maryland in the United States. It lies south of the Severn River, east of the Patuxent River, and north of the West River and Rhode River, and drains to the Chesapeake Bay. Total watershed area is 66 square miles (170 km2)(including water surface), 56 square miles (150 km2) (or 85%) of it land. From its headwaters in western Anne Arundel County in Crofton, the river enters the Chesapeake Bay south of the historic port city of Annapolis, hence the name South River. Its major non-tidal branches include the North River, which is the non-tidal portion of the South River, and Bacon Ridge Branch, which drains the area east of the North River. Their confluence is between Maryland Route 450 (Defense Highway) and US 50 (John Hanson Highway). Some of the creeks on its north shore drain highly developed portions of Annapolis, especially Church Creek, which drains much of the Parole and Annapolis Harbour shopping centers. The navigable portion of the South River is crossed by two bridges, one carrying Maryland Route 2 (Solomons Island Road), known as the South River Bridge, and the other carrying Riva Road, known as the Riva Bridge. A bridge carrying US 50 crosses its upper tidal reaches.

Quiet Waters Park is a park in eastern Anne Arundel County, Maryland, United States. It contains 340 acres (1.4 km2) and is operated by the Anne Arundel Recreation and Parks. It is open year-round. Organizations using the park include the Friends of Quiet Waters Park. As of 2010, it attracts 700,000 visitors a year.

The Severn River is a tidal estuary 14 miles (23 km) long, located in Anne Arundel County in the U.S. state of Maryland, south of the Magothy River and north of the South River.

The Maritime Republic of Eastport (MRE), commonly known as simply Eastport, is a seaside neighborhood community and tongue-in-cheek micronation located in Annapolis, Maryland in the US. The neighborhood was first settled in 1655, and became known as Eastport in 1888, before being annexed to Annapolis in 1951. In 1998, Eastport residents declared independence as a mock secession in response to the Maryland State Highway Administration's temporary shutdown of the drawbridge connecting Eastport to the rest of Annapolis. The micronation hosts numerous fundraisers, including an annual tug of war, 0.05 km (55 yd) run across the aforementioned bridge and annual "Burning of the Socks". The micronation is popular among tourists.