Old City Hall and Engine House

The Colonial Annapolis Historic District is a historic district in the City of Annapolis, the state capital of Maryland, that was designated a National Historic Landmark District in 1965 and was geographically further expanded in 1984.

George Washington's resignation as commander-in-chief marked the end of Washington's military service in the American Revolutionary War and his return to civilian life at Mount Vernon. His voluntary action has been described as "one of the nation's great acts of statesmanship" and helped establish the precedent of civilian control of the military. After the Treaty of Paris ending the war had been signed on September 3, 1783, and after the last British troops left New York City on November 25, Washington resigned his commission as commander-in-chief of the Continental Army to the Congress of the Confederation, then meeting in the Maryland State House at Annapolis, Maryland, on December 23 of the same year. This followed his farewell to the Continental Army, November 2 at Rockingham near Princeton, New Jersey, and his farewell to his officers, December 4 at Fraunces Tavern in New York City.Washington's resignation was depicted by John Trumbull in 1824 with the life-size painting, General George Washington Resigning His Commission, now on view in the United States Capitol rotunda.

The Maryland State House is located in Annapolis, Maryland. It is the oldest U.S. state capitol in continuous legislative use, dating to 1772 and houses the Maryland General Assembly, plus the offices of the Governor and Lieutenant Governor. In 1783 and 1784 it served as the capitol building of the United States Congress of the Confederation, and is where Ratification Day, the formal end of the American Revolutionary War, occurred. The capitol has the distinction of being topped by the largest wooden dome in the United States constructed without nails. The current building, which was designated a National Historic Landmark in 1960, is the third statehouse on its site. The building is administered by the State House Trust, established in 1969.

Government House, also known as the Governor's Mansion, is the official residence of the governor of Maryland. It is located on State Circle in Annapolis, Maryland, adjacent to the Maryland State House complex. The residence has been the home of the Governor since 1870; before that, from 1777 until 1870, Jennings House was the residence of the governors of Maryland.Government House was designed by Baltimore architect R. Snowden Andrews (1830–1903). Originally designed in the fashion of the time, with a Mansard roof and Italianate arched windows. the residence was converted in 1935–36 to its present Georgian style.

St. Anne's Episcopal Church is a historic Episcopal church located in Church Circle, Annapolis. The first church in Annapolis, it was founded in 1692 to serve as the parish church for the newly created Middle Neck Parish, one of the original 30 Anglican parishes in the Province of Maryland. It remains in use by the Parish of St. Anne, part of the Episcopal Diocese of Maryland.

The Annapolis Convention, formally titled as a Meeting of Commissioners to Remedy Defects of the Federal Government, was a national political convention held September 11–14, 1786 at Mann's Tavern in Annapolis, Maryland, in which twelve delegates from five U.S. states (New Jersey, New York, Pennsylvania, Delaware, and Virginia) gathered to discuss and develop a consensus on reversing the protectionist trade barriers that each state had erected. At the time, under the Articles of Confederation, each state was largely independent from the others, and the national government had no authority to regulate trade between and among the states. New Hampshire, Massachusetts, Rhode Island, and North Carolina had appointed commissioners, who failed to arrive in Annapolis in time to attend the meeting, and Connecticut, Maryland, South Carolina, and Georgia had taken no action at all. The convention also related to George Washington's plans concerning the waterways connecting the Potomac and the Ohio River.

John Callahan House, known previously as Pinkney-Callahan House when it was located on St. John Street, is a historic home in Annapolis, Maryland, United States. The brick home was constructed by John Callahan (c. 1754–1803), a prominent and wealthy Annapolitan who served as the Register of the Western Shore Land Office between 1778 and 1803, around 1785–90. It has been moved twice in efforts to prevent its demolition. In 1900–01, the house was relocated to St. John's Street and then to its present site on Conduit Street in 1972. The home features an unusual gable-end principal façade and a largely intact Georgian/Federal interior finishes. It once served as St. John's College Infirmary. It was first listed on the National Register of Historic Places on November 12, 1971 (NRHP Reference Number 71000365); after its relocation in 1972, it was listed again in 1973. It is a contributing property in the Colonial Annapolis Historic District.

The Historic Inns of Annapolis consist of three historically rich inns dating back to the end of the American Revolutionary War. The historical buildings, located in Annapolis, Maryland, include the Maryland Inn, Governor Calvert House, and the Robert Johnson House as well as the Treaty of Paris restaurant and the King of France Tavern, which are the on-site dining facilities. Managed by Remington Hotels, the hotel is located in the heart of the city of Annapolis, MD. The Historic Inns of Annapolis is a member of Historic Hotels of America, the official program of the National Trust for Historic Preservation.

Reynold's Tavern is an 18th-century tavern located at 6 Church Circle in Annapolis, Maryland. It is the oldest tavern in Annapolis, and one of the oldest in the United States. The building has been nominated to be included on the National Register of Historic Places.

The Banneker-Douglass Museum, formerly known as Mt. Moriah African Methodist Episcopal Church, is a historic church at Annapolis, Anne Arundel County, Maryland. It was constructed in 1875 and remodeled in 1896. It is a 2+1⁄2-story, gable-front brick church executed in the Gothic Revival style. It served as the meeting hall for the First African Methodist Episcopal Church, originally formed in the 1790s, for nearly 100 years. It was leased to the Maryland Commission on African-American History and Culture, becoming the state's official museum for African-American history and culture. In 1984, a 2+1⁄2-story addition was added when the building opened as the Banneker-Douglass Museum.It was listed on the National Register of Historic Places in 1973 and is within the boundaries of the Colonial Annapolis Historic District. Steven Newsome is the former director of the museum.The Banneker-Douglass Museum is a museum dedicated to preserving Maryland's African American heritage. Located at 84 Franklin Street, Annapolis, Maryland, the museum is housed in the old Mount Moriah A.M.E. Church. The museum is named for Benjamin Banneker and Frederick Douglass. The contributions of famous African American Maryland residents are highlighted, including Kunta Kinte, Benjamin Banneker, James Pennington, Frederick Douglass, Harriet Tubman, Matthew Henson and Thurgood Marshall. Other exhibits include black life in Maryland, and African and African American art. Lectures, workshops, performances and educational programs are offered each year. The facility serves as the state's official repository of African American material culture. The museum also has a library and archives.

Artisan's House is a historic home located at Annapolis, Maryland, United States. It is a 1+1⁄2-story frame house on a brick foundation representative of modest middle class dwellings of the 18th century. It was likely used as a barracks during the Revolutionary War. Because of this, it is also known as "Hogshead."It was listed on the National Register of Historic Places in 1973, and it is a contributing property in the Colonial Annapolis Historic District. Hogshead is owned by the Historic Annapolis Foundation and operated as an 18th-century period historic house museum with Colonial-era re-enactors.

The Upton Scott House is a historic home in Annapolis, Anne Arundel County, Maryland, United States. It is a 2+1⁄2-story, rectangular brick house. The interior is lavish, and the house has sustained only minor alterations in the 20th century. The house was built for Dr. Upton Scott, the personal physician to the Royal Governor of the Province of Maryland, and is of the transitional Georgian style. The house was built by William Brown, and closely resembles Brown's house on the South River, now known as the London Town Publik House.The Upton Scott House was listed on the National Register of Historic Places in 1975.