The county seat of New Madrid County has been New Madrid for much of the county’s history. However, from 1815 to 1822 the county seat was in a town that no longer exists—Winchester. Winchester was about a quarter mile south of present-day Sikeston. The location was in the region called the Grand Prairie—a low, elevated sandy grassland called the Sikeston Ridge today. Within a mile east of Winchester was the shore of St. Johns Bayou and the vast shallow lake or swamp, Lake St. John.
The Territorial Legislature passed laws setting up commissions to fix seats of justice and public buildings for individual counties. They enacted the law for New Madrid County on August 14, 1813, which named Samuel Cooper, Thomas Windsor, Daniel Sparks, John Guething, and John Tucker as commissioners. Some historians suggest that New Madrid’s county seat needed to be relocated because the town and courthouse had been heavily damaged by the series of earthquakes in 1812-1814. However, surviving records of the Circuit Court and Court of Common Pleas document that these bodies met in New Madrid until the end of September 1813, corresponding to creation of the commission to permanently locate a seat of justice.
The courts subsequently met at the houses of Samuel Phillips, then Jesse Bartlett, in the Grand Prairie from March 28, 1814, to June 15, 1815. Grand Prairie, according to court records, was “…selected as the most convenient place for holding the said Court by a majority of the commissioners appointed by the Legislature of this Territory…[and they] are authorized to appoint a Temporary place for holding said Court until said permanent seat be established ...” Placement of county seats in Missouri at that time favored sites near the center of the county to provide convenient access for residents. The site of Winchester was nearer the center of New Madrid County, which encompassed most of the Missouri Bootheel at the time.
The town became public property on July 8, 1815, when two deeds delineated the extent of the town. The site included three adjacent parcels: eighty acres from the west end of land originally granted to Claud Thiriot, a little over four acres from the east end of parcel of land granted to Solomon Armstrong, and a little over six acres from the head right of Joseph Hunot Junior. The first deed transferred ownership of the first two tracts from Samuel Phillips to Stephen Ross and Moses Shelby. The second transferred these two parcels and the third from Ross and Shelby to Daniel Sparks, Samuel Phillips, and Hugh Johnson, the Commissioners of the Seat of Justice and Public Buildings for New Madrid County. When Ross and Shelby deeded the land on July 8, 1815, Sparks was the sole remaining original commissioner and Samuel Phillips and Hugh Johnson received appointments to replace the others.
The name “Winchester” comes from a prominent local family. Some say it honors Col. Henderson Winchester, who lived nearby. Another Winchester, William, was a Judge of the Court of Common Pleas.
The town initially grew rapidly. Thomas Bartlett opened the first store in Winchester, and Hartwell Baldwin kept a tavern. David Hunter, Mark H. Stallcup, and Christopher Houts opened additional stores.
Winchester declined quickly after the county seat reverted to New Madrid in 1822. County boundary changes placed it almost in Scott County in 1821. If anything remained of the town by the time John Sikes founded Sikeston in 1860, there is no mention of it. Louis Houck stated the former town was a cornfield by 1908.
