Annapolis MD Annapolis is one of the oldest cities in the US, with many historic houses. This is the William Paca House, which dates to the 1760s. Hammond Harwood House, 1774. Chase Lloyd House, 1769. James Brice House, 1767, now under extensive renovation. Hogshead, early 1800s. Colorful row houses. Pinckney Street. Sculpture of Alex Haley, author of Roots. Ego Alley, where the people show off their yachts. Main Street. The Choptank. Sunset on Main Street.