The Colonial Annapolis Historic District is a National Historic Landmark covering the heart of the old city. Roughly 1,500 buildings dating from the 17th through 19th centuries survive here — an unusually high concentration for an American city of this size. The district is organized around two circles (State Circle at the top, Church Circle lower down) connected by Maryland Avenue, with a grid of brick streets running down toward the waterfront.
Walking the district takes about two hours if you stop to look at facades; longer if you take tours of the open houses. The concentration of colonial Georgian architecture is genuinely exceptional — the Hammond-Harwood House, the William Paca House, the Chase-Lloyd House, and the Maryland State House are all within a few minutes' walk of each other. In the evenings the restaurants and bars along Main Street and the City Dock fill up with a mix of Naval Academy families, Washington weekenders, and locals.