A datestone of 1752 is on the building. However, local architectural historians have argued it was built circa 1782, shortly after the American Revolution by Daniel Elliott who served in the war.
An account ledger from the Tavern exists at the Main branch of the Carnegie Library of Pittsburgh dated from 1793 to 1797.
The Tavern was continuously operated as a restaurant or bar (except during prohibition when it was operated as a "confectionary store") until 2009.
The Tavern is located at a bend in what was the historic Washington and Pittsburgh Turnpike, a toll road connecting Pittsburgh to Washington County and the National Road (Route 40). It is believed to have served as a tollhouse and frontier trading post and likely played a role in the Whiskey Rebellion, the late 18th century uprising against a federal excise tax on liquor, that ended with the implementation of martial law. "John Woods was in the tavern and used the owners' ferry the night before the raid on John Neville's estate" (July 16, 1794). Moreover, the ledger contains over 70 names connected with the Whiskey Rebellion.
Pittsburgh's Old Stone Tavern Friends Trust incorporated in December of 2013 with the mission statement "To secure Pittsburgh's Old Stone Tavern and its property, provide for its long term preservation, and educate the public regarding its significance in United States History".