Henry Caywood Prewitt, 86, died peacefully surrounded by his wife Linda, and his sons, Robert, Caywood and Tom, on November 24, 2017. Henry was born to Thomas G. and Elizabeth Caywood Prewitt in Mt. Sterling Kentucky. He was raised in nearby North Middletown. He attended Washington & Lee University and later the University of Kentucky where he obtained a law degree. Following graduation, he served in the JAG Corps in the U.S. Air Force. Upon his discharge he returned to Bourbon County where he began a successful private practice which spanned 60 years. During that time he advised individuals, businesses and governmental agencies on a wide variety of issues. He served as circuit judge in Bourbon, Scott and Woodford Counties. He helped found and eventually served as chairman of the board of Bluegrass Savings & Loan in Paris. He previously served as a deacon, trustee and elder at the First Presbyterian Church in Paris. He was a member of the Permanent Judicial Commission of Transylvania Presbytery. He was chairman of the Democratic Party in Bourbon County for many years and remained active in local, state and national politics. He was a member of the Lexington Club and the Keeneland Club. He is preceded in death by his wife of forty five years, Margaret Cliff Prewitt and is survived by his wife, Linda Lehmann Prewitt; sons, Robert C. Prewitt (Martha), H. Caywood Prewitt , Jr. (Beth), Thomas A. Prewitt (Jamie); Chuck Cassagne, Cristal Cassagne, Chris Cassagne; grandchildren Taylor Prewitt, Baker Prewitt, Madison Fogarty, Quentin Prewitt, Henry (Woods) Prewitt, III, Jerah Johnson, Mark Taylor, Van Taylor; and great grand-children, Coralie Johnson and Collin Johnson. Visitation: Monday, November 27 from 1-3:00 pm at the Mt. Horeb Presbyterian Church, 2793 Iron Works Pike in Lexington. Service will follow at 3:00 pm. A reception will be held at the Lexington Club, 170 Esplanade, Lexington at approximately 4:30 pm. Henry will be interred in North Middletown at a later date. Memorials suggested to Mt. Horeb Presbyterian Church or St. Joseph Hospital Foundation.