He was also active in several businesses, including managing the L. J. Morton store in St. Albans, and a vice president of the Franklin County Savings Bank and Trust Company and the St. Albans Cooperative Savings and Loan Association. In 1926, he received his qualification as a certified public accountant. From 1931 to 1932 he served on the Vermont Public Service Commission, and from 1932 to 1938 he was the commission's chairman. He received the honorary degree of LL.D. from Norwich University in 1934. In April 1938, Cushing was appointed a judge of the Vermont Superior Court. He advanced by seniority to become the chief judge in 1949, and he served on the court until 1952. In January 1952, Cushing was appointed as an Associate Justice of the Vermont Supreme Court, filling the vacancy caused by the death of Samuel H. Blackmer. He remained on the court until June 1953, when he resigned because of ill health, and was succeeded by Paul A. Chase. He died in St. Albans on September 23, 1957. He was buried at Greenwood Cemetery in St. Albans. In 1912, Cushing married Bessie Morton of St. Albans (1883-1961), the daughter of Leonard J. and Emma Morton. They were the parents of a son, Morton (1921-1963).