Middleton Tavern, Annapolis

Located in Downtown’s City Dock, just a block from the United States Naval Academy, Middleton Tavern is a testament to both of these local story lines. Established in 1750 by Horatio Middleton, this is one of the oldest continuously operating taverns in America. It started off as an “inn for seafaring men”, providing base for Middleton’s Ferry Service which linked Annapolis to Maryland’s Eastern Shore, and thus served as the meeting site for many historic personalities.

Tench Tilghman took the ferry to deliver news of Cornwallis’ surrender in 1781, while Thomas Jefferson used it en route to Rock Hall in 1783, whereas George Washington took it on his way to…somewhere, too. After Middleton’s death, his son expanded the family business to include ship building and overseas trade. During that time, the tavern enjoyed some of its most sensational customers. Practically next door to the Maryland State House, members of the Continental Congress came to this joint after the ratification of the Treaty of Paris and the official end of the Revolutionary War in January 1784.

James Monroe, a friend of the elder Middleton, may have even visited the tavern in 1818 as a sitting president. The bar’s history throughout the rest of the 1800s is a little hazy, but in 1968, the current owner, Jerry Hardesty, bought and restored the property. In 1983, he expanded the restaurant to include the new Tavern and Oyster Bar.

Void of the surrounding gardens, which, back in the old days, stretched from Prince George Street to the water, Middleton’s front porch today provides some of the greatest people watching in town. Paired with some fresh regional seafood from the raw bar and a Category 3 Dark and Stormy, it creates recipe for a fantastic evening in Annapolis. The tavern's specialties include Maryland crab cakes, rockfish, oysters, and clams. Middleton’s Electric Lemonade (Smirnoff Citrus Vodka and Blue Curaçao mixed with the Tavern’s homemade lemonade) is a separate attraction.

Other than the great food and drink served with a slice of history, this 18th-century Georgian establishment also hosts some truly magnificent live music events: acoustic blues, piano, jazz and anything else to make you feel great. Their famous Piano Bar on Friday and Saturday nights are particularly not to be missed!