He was awarded a silver medal by the Confederation Congress for his leadership at the Battle of Cowpens in 1781,[1] during which he commanded the 2nd Maryland Regiment.

"[6] At the conclusion of the war, Colonel Howard was admitted as an original member of the Society of the Cincinnati of Maryland.

He subsequently joined the newly organized Federalist Party and was elected to the Senate of the Fourth Congress by the General Assembly of Maryland to serve the remainder of the term of Richard Potts, who had resigned.

[citation needed] In 1798, amidst rising tensions with France, Howard declined a commission as brigadier general in the United States Army.

[1] At the end of his Senate term in 1803, Howard returned to Baltimore, where he avoided elected office but continued in public service and philanthropy.

[10] In the 1816 presidential election, he received 22 electoral votes for Vice President[2] as the running mate of Federalist Rufus King, losing to Democratic-Republican candidates James Monroe and Daniel D. Tompkins in a landslide.