This is just my opinion based on the research I have done regarding Oktibbeha County. I would think you could probably get a compy of the Cemeteries of Clay County publication from their Genealogy Socitey and find many graves going back to the early 19th Century in Greenwood Cemtery, West Point Mississippi.
Judge Thomas Battle Carroll cites the missionaries at the Mayhew mission as being among the first Whites in the area. However, the Mayhew Mission is at the extreme Northeastern tip of present day Oktibbeha County and I am not sure whether portions of the grounds actually lie in present day Clay County. I know the State historical marker is off Highway 45 just south of the West Point City limits. Another tricky part of the question as it pertains to Clay County is that no one lived in Clay County prior to the 1870s when it was formed from several surrounding Counties, Choctaw, Lowndes, and Oktibbeha being the major donors.
In Mississippi Memoirs, (I cannot recall the source reference) the description of the formation of Oktibbeha County indicates that there were many of the original patent holders present in 1833-34. John Wesley Gilbert and family purchased a patent in Northeast Oktibbeha County in 1846, but had lived in Monroe County in the 1840 Census. All indications are that family entered the area around 1844 when their daughter Laurania was born.
Palo Alto was established in 1846 and incorporated in 1852. It declined after the war when most commerce moved to Abbott Mississippi. Judge Carroll devotes some part of his book to discussing the canals along northern Oktibbeha County, especially the Trimcane. In association with Tibbee Creek the Trim Cane Canal was perhaps one of the major avenues of Commerce during the first half of the 19th Centurys. Many families lived along that water system which passed just south of West Point en route to the Tombigbee.
Along that major commerce route, many families established what eventually became a huge plantation society. The family names include the Barksdales (1841), Gilberts (1846), Prices (1850), Suddeths, Muldrows, Osborns, Reeses (1841), Clarkes (1838), Billingtons (1841), Greers (1838-1843), and others. Many of the land patents attributed to Clay County were filed between 1838 and 1841 which means they were obviously initially tied to the original Counties.
Judge Carroll also points out that when most white settlers arrived in Oktibbeha and Clay County, they found an already established infrastructure of roads, plantations, and commerce. If one were truely looking for the first families they should probably start looking in the Choctaw and Chickasaw Tribes for the original residents. The Kellum Family in Oktibbeha County has a land deed purchased from a Choctaw family around the time the county was formed.
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