Miles taught school in Albany and
Craftsbury, and
studied law with attorneys Charles I. Vail and
William W. Grout. He was
admitted to the bar in 1872, and practiced in Albany and Craftsbury. A
Republican, he held local office in both towns, including serving as school superintendent in Albany in 1867 and Craftsbury in 1876, and Craftsbury Town Clerk from 1875 to 1881. From 1872 to 1874 he represented Albany in the
Vermont House of Representatives, and he represented Craftsbury in the Vermont House from 1878 to 1880. In 1881, he moved to
Barton, where he practiced law in partnership with Grout. When Grout retired in 1888 in order to devote full time to his duties as a member of the
United States House of Representatives, Miles continued the practice on his own. From 1890 to 1894, Miles served as
State's Attorney of
Orleans County, and from 1894 to 1896 he represented Orleans County in the
Vermont Senate. In 1904, Miles was elected to represent Barton in the Vermont House; when
Clarke C. Fitts resigned as a Representative to become
Vermont Attorney General, Miles took his place as chairman of the House Judiciary Committee. ==Career as a judge==