Dr. Caleb Winfrey graduated from the Medical Department of St. Louis University in 1847 and settled in Lone Jack, Missouri, where he set up his medical practice. In 1861 he enlisted as a surgeon in the Missouri State Guard, and accompanied Colonel Gideon Thompson to Cowskin Prairie. He was present at the battles of Wilson’s Creek and Lexington. Returning to Lone Jack in 1862, he helped organize a Confederate company and commanded it at the Battle of Lone Jack, quite literally fighting in his own backyard.
After Lone Jack he was the senior surgeon for Joseph Shelby’s Brigade, and was present at the battles of Cane Hill, Prairie Grove, Newtonia and Springfield.
In the autumn of 1864 he accompanied General Sterling Price on his Missouri raid. At the Battle of Westport, Dr. Winfrey, at the request of Price, remained behind to care for the wounded and dying.
After the war Dr. Winfrey returned to a private medical practice at Pleasant Hill, Missouri.
Image Courtesy Wilson’s Creek National Battlefield; WICR 31591
