[9] During the War of 1812 the Chesapeake Bay was a major route for British War ships, who established a naval and military base at near-by Tangier Island in Virginia for the Royal Navy under Rear Admiral George Cockburn with Fort Albion there, which constantly raided Chesapeake Bay waterfront towns, villages and farms and scattered community residents, and also eventually attacked and burned Washington, D.C., and unsuccessfully attacked the City of Baltimore during 1813 and 1814.

During the War of 1812, a local citizen militia in St. Mary's County established a clandestine base on Point Lookout to monitor movements of British warships on Chesapeake Bay.

The militia also established a secret nighttime system of post riders to send intelligence reports from Point Lookout to Washington, D.C., in order to keep President James Madison up to date on British movements.

St. Mary's County's roads were notoriously rough at the time, and the trek by horse was more than 80 miles, so a relay system was set up, passing messages from one rider to the next.

This had the effect of blinding American intelligence efforts in the region, and is thought to have contributed to the eventual Burning of Washington in August 1814 by British troops.

President Madison and United States Secretary of War, John Armstrong, Jr. was later faulted for not aiding the militia in Point Lookout.

[9] According to the Maryland Department of Natural Resources, of the 50,000 soldiers held in the army prison camp at Lookout Point, all of whom were housed in tents, nearly 4,000 died.