John Riddle was born January 1 1809, which was then Mississippi Territory. His father was William Riddle who died n 1818, and his stepfather was John Jones. John’s mother’s name was Caty. John’s father, William Riddle, was a white man, his mother was Choctaw, therefore John Riddle was half-Choctaw. The Presbyterian missionaries had brought religious teachings to the Choctaws at an early time, certainly by 1805, as we find in the MISSIONARY HERALD papers. There are accounts of the missionaries who came from the east, coming to eh Ohio River, and down the Mississippi and making the entire journey by water. By 1810 we find the Choctaws giving up their practice of marrying two wives, and sincerely trying to educate their young male children. Education their young children was sometimes accomplished through the missions. The children would attend school for a term or so, and then return to their people and teach them what they had learned. Therefore a child was much older when attending school than we find today.
In 1825, we find John Riddle attending the Choctaw Academy located in White Sulphur Springs, KY. We also find John attending the KY Academy in 1830. (a-20 through a-26). Also attending school, we find John’s brother, William Riddle, along with the Pitchlynns, Folsoms, Gardners, all very familiar names which will have interest in our lineages as we go along. John was married to Eve S. Pitchlynn in 1830, and was twenty-one years of age. In October 1837, we find John Riddle as an Interpreter. (a-27) On the Choctaw Muster Roll dated 8 Nov 1837 we found Robert M. Jones, Chief, and John Riddle, Interpreter. There were about 485 men in all, or ten company’s total Robert M. Jones, Chief, and John Riddle, Interpreter, along with forty-seven Warriors, constituted One Unit of men. If you will refer to “a-27”, John Riddle’s War Record was obtained from the National Archives in Washington, D.C. So between the years of 1837 and 1841, John Riddle came to “new Indian Territory West”, along with Eve who was his wife, and their first five children.
Between the years of 1830 and 1850, the migrations began. The Choctaw people first settled along the major rivers and creeks nearest to Arkansas, but as their population increased they moved father west. Preparing for the emigration of the Chickasaw, from Mississippi to their new home in the West, land was purchased from the Choctaws fro the Chickasaws. In order for the Chickasaws to reach their new land, they had to cross Choctaw land, coming from Skullyville to Boggy Depot. This was a heavily traveled trail, which later became the proposed route to the Butterfield Stage, from St. Louis to San Francisco. This trail is important to the Riddles, as the route led through John Riddle’s land. The Pony Express was the mail service for the years 1830 to 1850, and very expensive mail service, indeed, as reported by editor Daniel Folsom in the CHOCTAW TELEGRAPH, a newspaper published at Doaksville, OK.