Availability Search

One of the oldest continuously operating taverns in America, Middleton Tavern of Annapolis, Maryland cordially invites you for a slice of history to be served with delicious regional seafood such as Maryland crab cakes, rockfish, oysters, and clams. It’s also a great place for music, offering up “Annapolis Unplugged” for local talent on Wednesday nights, along with bands downstairs and a piano bar upstairs Friday and Saturday nights.

Colonial & Revolutionary History

Middleton Tavern hosted many of our country’s most admired leaders during the post-war period after the American Revolution. Among its most distinguished guests were George Washington, Benjamin Franklin, and Thomas Jefferson. It was also frequented by members of the Continental Congress.

A hub for Annapolis’ early social scene, Middleton Tavern was where the Maryland Jockey Club, Free Masons, and the renowned Tuesday Club, whose members were many of the city’s most prominent intellectuals, met regularly to drink, smoke, gamble, and foster camaraderie.


Horatio Middleton acquired the property in 1750, and he subsequently made the building into an “Inn for Seafaring Men”, naming it Middleton Tavern. A consummate businessman, Middleton was also the owner of a ferry linking Annapolis to Chesapeake Bay’s Eastern Shore.

After his death, the tavern was operated by his widow Anne. His son, Samuel Middleton, eventually took over while continuing to manage the ferry service. As a result, the site became a key stop for early travelers. The grounds were considered an Annapolis showplace because its gardens stretched from Prince George Street all the way to the waterfront.

Current Ownership

When the current owner, Jerry Hardesty, purchased the building in 1968, it was known as the Mandris Restaurant. Hardesty undertook a full restoration of the interior and exterior and reinstated the original name of Middleton Tavern. More remodeling and expansion was done in 1983, and the result was a revitalized tavern with a new Oyster Bar. The expanded and improved upstairs dining room areas made the accommodation of private parties, meetings, and large weekend crowds possible.

For More Information: Middleton Tavern

Address: 2 Market Space, Annapolis, Maryland 21401

Telephone: (410) 263-3323

Your Inn Near Middleton Tavern

Middleton Tavern is a very short walk away from Gibson’s Lodgings, a historic inn located in downtown Annapolis. Call us to reserve your room at our toll free number (877) 330-0057. We’ll be very happy to serve you and your family throughout the year.

Comments are closed.