Ross was Treasurer of Passumpsic Savings Bank from 1858 to 1868. He practiced law in St. Johnsbury until 1870. After being State's attorney for Caledonia County from 1862 to 1863, he was appointed a member of the State board of education, holding that office from 1866 to 1870. From 1865 to 1867, Ross was a member of the Vermont House of Representatives and he was a State senator in 1870. He was a member of the State Board of Education from 1866 to 1870 and served on the Vermont Council of Censors in 1869. He was judge of the Vermont Supreme Court from 1870 to 1890 and Chief Justice of Vermont from 1890 to 1899. In December 1898, U.S. Senator Justin S. Morrill died. Governor Edward Curtis Smith offered to appoint Benjamin F. Fifield to the vacancy, and Fifield tentatively accepted. Several days later, Fifield declined, and Smith then offered the appointment to Ross, who accepted. He served from January 11, 1899 to October 18, 1900, when a successor was elected. While in the Senate, he was chairman of the United States Senate Committee to Examine Branches of the Civil Service. He was not an active candidate for reelection in 1900. In October 1900, Ross was elected president of the Vermont Bar Association, and he served a one-year term. In November 1900, he succeeded David J. Foster as chairman of the state board of railroad commissioners, and he served until being succeeded by Fuller C. Smith in November 1902.
Death and burial
Ross retired to his home in St. Johnsbury, where he resided until his death. He died on February 23, 1905 from injuries sustained when his sleigh was struck by a train a few days earlier. According to published accounts, Ross and his wife were stopped at a crossing while a train passed by. Their horse became frightened and dashed between two train cars, demolishing the sleigh and killing Mrs. Ross. The train crew transported Ross to the hospital, where he was diagnosed with a broken hip and other injuries, and remained until his death. Ross is interred at Mount Pleasant Cemetery in St. Johnsbury, Vermont. His wives are buried at either side of his grave.
Family
Ross married twice. He married Eliza Ann Carpenter on November 22, 1852. They were the parents of eight children, including Caroline C., Eliza M., Helen M., Julia, Martha E., Edith Helen, Edward H., and Jonathan C. In 1887, he married Helen Daggert, and they remained married until her death.