Howard graduated from Plymouth State College in 1978 with a B.A., and he received a J.D. from the Georgetown University Law Center in 1981. After law school, Howard was an attorney in the New Hampshire Attorney General's Office, rising to become Deputy Attorney General, before joining the federal government as the United States Attorney for the District of New Hampshire in 1989. He left that position in 1993 to become the New Hampshire Attorney General. He served as Attorney General until 1997 when he entered private practice, which he continued in until his appointment to the First Circuit.