In 1937 Furcolo moved to Springfield, Massachusetts, where he opened a law practice. He specialized in criminal and civil trial work, and quickly rose in prominence, the quality of his legal preparation and trial work receiving favorable notice from others in the legal community. After a few years he moved his growing family to neighboring Longmeadow. He made his first bid for public office in 1942, an unsuccessful run for district attorney. During World War II he served in U.S. Navy as a lieutenant (junior grade) aboard , a transport vessel in the Pacific, which participated in the Invasion of Okinawa.