From 1796 through the mid-19th century, the building provided a focus for community activity in Georgetown serving as a site of community meetings, business functions, and transportation. The City Tavern has undergone three major alterations including the filling in of the original carriage way after the Civil War, exposure of the basement portion of the building when M Street was lowered in the 1870s, and a major restoration of the property in 1961. Because the first two changes are common for Georgetown buildings and the latter was based on extensive documentation, none of the changes have affected the overall form and integrity of the building.
The City Tavern was at the crossroads of early capital and national history. Its first proprietor was Clement Sewell, who served as innkeeper until 1799. Charles Mclaughlin followed until 1801, then Joseph Sermes until 1805. Sermes operated under the sign of the Indian King and established it as a stop on stage routes to and from the Federal City.
The tavern has close associations with Jefferson and Adams. Jefferson's letters reveal that he held the place in high regard and that he recommended it to important visitors. Plans were laid here for greeting John Adams in 1800 as he arrived at the District boundary and was escorted to the White House by Georgetown citizens.