Kuykendall first practiced law in Greensboro, North Carolina, before establishing a law practice in Romney, West Virginia. He was elected to represent Hampshire County in the West Virginia House of Delegates for one term in 1906 and another term in 1918, each consisting of two years. He was the mayor of Romney for three terms, and in 1922 he served as Romney's city attorney. Kuykendall was elected to three terms as a member of the Hampshire County Board of Education; he also served as a Chancery Commissioner for the county. During World War I, Kuykendall was a member of the Legal Advisory Board of Hampshire County; he also participated in Liberty bond drives and directed sales to raise American Red Cross funds. Kuykendall was engaged in the management of a commercial peach orchard near Romney known as Sherman Orchard. He died in 1928 and was interred at Indian Mound Cemetery in Romney.
