Middleton Tavern was host to a galaxy of the nation's most revered leaders during the period following the American Revolution. George Washington, Thomas Jefferson, and Benjamin Franklin were numbered among their prominent patrons.
The Tavern was frequented by members of the Continental Congress meeting in the State House on such historic occasions as the resignation of General Washington's commission, December 23, 1783, the ratification of the Treaty of Paris ending the Revolutionary War in January 1784, and the Annapolis Convention which laid the groundwork for the Federal Constitution Convention held the following year in Philadelphia.
It is also probable that James Monroe, who knew Middleton as a Virginia delegate to the Continental Congress, visited the Tavern after his election to the Presidency. When President Monroe was received in Annapolis for his stay from May 28-30, 1818, he was greeted by Annapolis Mayor John Randal, who, at the time, was the owner of the Tavern.
In addition, Middleton Tavern was the site of meetings of the Maryland Jockey Club and Free Masons, as well as the renowned Tuesday Club, whose membership was made up of some of the town's most distinguished wits, and which met for the purpose of drinking, smoking, gambling and comradeship.
The building was probably occupied as early as 1740. In 1750, Elizabeth Bennett sold the property to Horatio Middleton who operated the building as an "Inn for Seafaring Men." The nautical oriented Middleton also owned a ferry that linked Annapolis to the Eastern Shore of the Chesapeake Bay.
Following the death of Horatio Middleton, the Tavern was operated by his widow, Anne, and later by his son, Samuel Middleton, who also continued to operate the ferry boats as well as an overseas trade operation and ship construction business - all from the Tavern site.
The Tavern was an all important stopping place for early travelers using the ferries to cross the Bay, including George Washington; Tench Tilghman, on the way to Philadelphia with the message of Cornwallis' surrender at Yorktown; and Thomas Jefferson, whose records note that in 1783 he gave Samuel Middleton passage money to Rock Hall on the Eastern Shore.
In those days, Middleton's was much more than a tavern; it has been described as one of the early showplaces of Annapolis, with its gardens spreading form Prince George Street to the water's edge.
During the Revolution, the Tavern was operated by George Mann, but when the war ended, Samuel Middleton's son Gilbert, operated the business until the 1780's. The next owner was John Randall, a distinguished Revolutionary logistics officer who, prior to the war, was a builder and a partner to the renowned architect William Buckland, designer of Annapolis' Hammond-Harwood House.
Jerry Hardesty, the current owner of Middleton Tavern, bought the restaurant in 1968 from Cleo and Mary Apostol who had operated the Mandris Restaurant on the corner for thirty-five years. Hardesty restored the building inside and out and was responsible for changing the name back to the original Middleton Tavern.
In 1983, Middleton Tavern underwent remodeling and expansion, which resulted in the new Tavern and Oyster Bar. The greatly expanded and beautifully appointed upstairs dining rooms allow the Tavern to accommodate private parties, meetings and the heavy weekend crowds.