With the war also came suffering and tragedy, as the United States was thrust into a conflict for which it was barely prepared. Its hastily-organized armies were routed by the British, who had the most powerful army and navy in the world. On August 24, 1814, the county was dealt the ultimate defeat, when the national capital was captured and burned.

For Marylanders, the war came in February 1813, when the British sailed into the Chesapeake Bay and began a campaign to terrorize the coast. In Annapolis, the next two years were a time of anxious watching and waiting.

Annapolis was never attacked during the war, but its residents expected to be at any moment. Contemporary records tell of a city, in the spring and summer of 1814, deserted by its inhabitants, including the governor himself. The British fleet was clearly visible out in the Bay and was closely watched by people like William Barney, standing on the dome with his “excellent glass.”

While the residents of the town watched the activities of the fleet with anxiety, the local enslaved population saw an opportunity for escape. Twenty-one slaves, including 20 belonging to Maria Margaret Ogle, rowed out to HMS Menelaus and other ships anchored off of Annapolis. In the end, some 700 Maryland slaves escaped to freedom, including 21 from Annapolis.