Caleb Winfrey was born in Surry County, North Carolina on December 8, 1823. Winfrey moved to Chapel Hill, North Carolina when he was nineteen. Winfrey graduated from the medical school at St. Louis University in 1847. Winfrey got married and started a medical practice in Lone Jack, Missouri. By 1861, Winfrey “had a lucrative practice, owned a large farm, and was proprietor of a drug and general store at Lone Jack.”
In 1861, Dr. Winfrey enlisted as a surgeon in the Missouri State Guard. In this capacity, Winfrey participated in the Battle of Wilson’s Creek and Lexington. During the summer of 1862, Winfrey and fellow Lone Jack resident, George B. Webb, recruited what would become Company C in the 12th Missouri Cavalry, commanded by Col. Upton Hays. Winfrey was elected the company’s captain with Webb as first lieutenant. Before the regiment was formally organized, it fought in the Battle of Lone Jack, during which Captain Winfrey led a charge to dislodge Federals from his house and store. After the first attack failed, Winfrey led a second attack and successfully drove the enemy from the structure. After organization, Winfrey was appointed regimental surgeon with the rank of major. Webb succeeded Winfrey as company captain of Company C.
Dr. Winfrey later became surgeon for the Iron Brigade commanded by Col. Jo Shelby during which he participated in the Battles of Cane Hill, Prairie Grove and Newtonia. Following the Second Battle of Springfield, Dr. Winfrey stayed with the Confederate wounded taken prisoner, accompanying them to City Point, Virginia. After being exchanged, Winfrey reached Camden, Arkansas and resumed his service. Following the Battle of Westport, once again Dr. Winfrey remained behind with the Confederate wounded. The war ended before he could rejoin his command.
After the war, Dr. Winfrey settled in Pleasant Hill, Missouri, and resumed his practice of medicine.
Matthews, Matt, and Kip Lindberg. “‘Shot All To Pieces’ The Battle of Lone Jack, August 16, 1862.” North and South 7, no. 1 (January 2004): 56–72.
McGhee, James E. Guide to Missouri Confederate Units, 1861-1865. Fayetteville, AR: University of Arkansas Press, 2008.
Webb, William L. “Dr. Caleb Winfrey.” In Battles and Biographies of Missourians, or, the Civil War Period of Our State, 328–30. Kansas City: Hudson-Kimberly Pub. Co., 1900.