Maryland

Annapolis

Middleton Tavern

In 1750, Samuel Horatio Middleton took over this building, the oldest building in Annapolis, from a Mrs. Bennett and established an Inn for seafaring men. It was only one of several enterprises operated by the entrepreneurial Middleton.

He also ran a ferry linking Annapolis to Rock Hall on the Eastern Shore. The ferry offered a popular shortcut on the route from Virginia to Philadelphia. George Washington, Thomas Jefferson, James Monroe, and Benjamin Franklin all recorded stops here in their journals.

Taverns in the 18th century were far more than a place to have a quick brew. A portside establishment was the place where one would catch up on news from the outside world, hears about the latest imports and fashions, and congregate with friends.
After his death, his son, Samuel owned and operated the inn. Many famous historical personalities stayed at the tavern, including Thomas Jefferson, Benjamin Franklin, and the founder of our country George Washington. It is unsure who else walks the halls of the tavern, which is currently a restaurant and bar But, but there are many strange and unexplained occurrences that seem to point to ghosts.

Often, plates fly across the room and glasses fall off the bar as thought someone is pushing then off one by one. On one occasion a table filled with empty dinner plates topples over even though no one is near it. Once, a restaurant employee witnessed a man in period clothing staring out onto the harbor, as though he was waiting for his ship to come in, and then as fast as the man appeared he disappeared. Shadows move across the rooms, and lanterns mounted on the walls turn upside down without any rational explanation.

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