Alfred H. Littlefield began his career in retail before transitioning into manufacturing, where he became a partner and president of Littlefield Manufacturing Company. He co-founded the Pawtucket Hair Cloth Company and held leadership roles in various business sectors, including banking and public utilities. Littlefield served in the Rhode Island Militia, rising to the rank of colonel, and later engaged in local politics, holding multiple positions in the Lincoln Town Council, Rhode Island House of Representatives, and Rhode Island Senate. His tenure as governor was marked by the establishment of the boundary line between Rhode Island and Massachusetts.

Alfred H. Littlefield's political identity is marked by a blend of industrial pragmatism and regional protectionism, as evidenced by his unexpected legislative alliances on environmental regulations. His deep-rooted business background in manufacturing and banking informs a highly localized approach to governance, balancing economic growth with community interests. Littlefield's military service and subsequent political career reveal a calculated strategy that prioritizes stability and regional influence over ideological rigidity.