August 1814, the third year of "Mr. Madison's War"
Great Britain's Royal Navy had dominated the Chesapeake Bay since their arrival in February of 1813. It could be said that the Bay was a British lake and it would remain so until March of 1815. With the mobility afforded by a fleet, the British came and went as they pleased, raiding small ports and towns throughout the Bay. They had already made several raids close to Baltimore including a trip up the Patapsco to take soundings to check depths of water approaches. Baltimore was of particular interest to the British, much more so than Washington, D.C. as many thought. It was the home port of many privateers, vessels which preyed upon British shipping in the Chesapeake Bay and on the high seas. For this reason, Baltimore had been dubbed a nest of pirates by the British.
After their success in Washington, the British now turned their attention to Baltimore. Having met only light resistance from militia forces at the Battle of Bladensburg on August 24, 1814, British Major General Robert Ross had little regard for them. To him, it seemed that very little had been done by Americans to stop the British from marching 50 miles across the state of Maryland and burning the capitol of the United States in late August. Considering the weak defenses, the British commanders no doubt thought that taking Baltimore would be just as easy.
General Ross had good reason to be overly confident. Of the four regiments he commanded -- the 4th, 21st, 44th and 85th -- three were veterans of the Peninsular War in Spain and had helped Wellington defeat Napoleon earlier that year. (The 21st Regiment came from Italy). These veterans were nicknamed Wellingtons Invincibles. Also placed at Ross' disposal were sailors and Royal Marines. Most of the military forces of the United States were up on the Niagara frontier with Canada. So it seemed likely that these British veterans would face only raw, untrained State militia troops when the attack on Baltimore came.
The defensive preparations around Baltimore had been underway for some time in 1814. This foresight and preparation was due in large part to Maj. Gen. Samuel Smith, a veteran of the Revolutionary War, who was in charge of the citys defenses. He had been planning for a British attack for months and when that attack seemed imminent, his men were ready. Smith knew that the only viable way for the British to attack Baltimore was by approaching the city from the east, by way of the North Point on the peninsula known as "Patapsco Neck". Smith organized both civilians and militiamen to work on the defenses. Ordinary citizens of the city and volunteers from neighboring states helped dig a system of earthen defenses. These stretched from the inner harbor (near modern Canton) to Hampstead Hill (area of present day "Patterson Park") and beyond.;