Middleton Tavern has stood at the foot of Main Street since around 1750, making it one of the oldest continuously operating taverns in the United States. The original proprietor, Horatio Middleton, ran a ferry service across the Chesapeake from the dock outside; later customers included George Washington, Thomas Jefferson, Benjamin Franklin and James Madison, all of whom dined here on their travels between Philadelphia and points south.
The building survived a major fire in 1972 and was carefully restored. The menu is solid Chesapeake — cream of crab soup, oyster shooters, soft-shell crab in season — and there is a raw bar upstairs and live music most weekends in the cellar. It is touristy and a bit pricey but worth one meal for the history alone.
Address: 2 Market Space, Annapolis, MD 21401. Tel: (410) 263-3323.