After the devastating earthquake of 1811 and repeated flooding of the Mississippi, the court chose an inland site for the county seat. According to an 1888 account, court convened in March 1814 in Big Prairie, and the seat of justice was located in Rossville, just south of present-day Sikeston, on a 50-acre site donated by Stephen Rose and Moses Hurley. Lots were sold to build a jail in 1817, which also served as a meeting place. County Court records in 1817 mention courts convening in the courthouse, and a page in the 1817 County Record has a simple drawing showing the jail in the center of a square and an intended courthouse at the edge. But there is no indication that a courthouse was built at Rossville.Winchester, also in the neighborhood of Sikeston, was identified in the records as an early county seat. Securities for three commissioners of the courthouse and jail were made October 24, 1817, and according to the County Record, court was held April 12, 1819, at the courthouse in Winchester.
Two years later, in May and August of 1821, court met in a home, and the sheriff was ordered to take possession of the courthouse of New Madrid county in Winchester and superintend repairs. The public property in Winchester was ordered to be sold to the highest bidder on May 14, 1824, but county records do not mention the courthouse.
The seat of justice moved to New Madrid February 4, 1822; commissioners were appointed for the courthouse and jail on May 13, 1822. This courthouse has been reported as one of the first frame buildings in the county; the others presumably were of log construction. According to Wetmore's Gazetteer of 1837, all the buildings in New Madrid were frame to hold up against the continued shaking of the earth after the New Madrid earthquake of 1811.
On November 17, 1848, the court ordered the disposal of the public square and the courthouse to help defray expenses for a new courthouse and square. A similar order appeared June 11, 1852, but apparently the courthouse was not sold until October 3, 1854.
For the new courthouse, ordered June 11, 1852, the court changed the location, appointing Robert Hatcher to select the site by purchase or donation. The cost was not to exceed $2,000. Apparently Hatcher failed to act; the court then appointed Thomas J. O. Morrison to replace him in February 1853. More problems followed, with one contractor forfeiting bond. Work was eventually completed; Morrison recommended the court receive the building November 13, 1854, reporting an expenditure of $2,950.
On March 17, 1875, five commissioners were appointed to select a new site for relocating the courthouse and other public buildings. The courthouse reportedly had been moved three times to escape the encroaching river.
Fire, however, rather than flood, finally destroyed this courthouse on September 24, 1905. A contemporary news account of the fire described the building as a one-story frame, constructed of red cypress, with a small door in the north gable above the porch. There were two offices on the south end, two on the north, with a courtroom in the middle.
No known photographs exist of any 19th century New Madrid courthouses. After the fire, county offices moved into several different buildings in New Madrid. Lilbourn, a few miles west of New Madrid, challenged for the county seat in 1912, but by vote New Madrid remained the people's choice.
For the 20th century courthouse, New Madrid County purchased a new site north of the original town in March 1915. From architects who presented plans, the court selected those from H. G. Clymer of St. Louis. Clymer's plan was for a brick building 107 by 75 feet with stone trim (see Figure 2). The court accepted the Interstate Building and Construction Co.'s bid of about $80,000 for the shell. Citizens donated $20,000 to supplement the $50,000 bond issue. Cornerstone ceremonies were July 4, 1915. Additional funds for finishing the courthouse and jail were authorized early in 1917, but no bids were received. World War I was beginning, and the labor force was reduced. Finally, W. W. Taylor, a master builder from Cape Girardeau, superintended final interior work, which was completed in January 1919. Final costs exceeded $100,000. This courthouse continues in use as New Madrid's seat of justice.