This is a piece I wrote for a webpage about thirteen years ago:
The topography of Randolph County began to take its present shape soon after the withdrawal of the glaciers of the last ice age. On the northern edge of the rolling hills north of the Missouri River, what would become Randolph County was covered by hardwood forests and plains grasslands. Large granite boulders left by the glaciers spoted the hillsides here and there. Sometime around 10,000 to 7,000 years ago, the first humans arrived. They hunted the wooly mammoth, mastodon, and other now extinct creatures. The area was rich in elk, wild turkeys, bear, buffalo, and deer. Around 800 CE and again around 1400 CE some of these early inhabitants carved the thunderbird on the entrance of a cave in what is now Camp Thunderbird near Cairo. Later the Missouri Indians used Randolph Co. as their hunting grounds. When white settlers first arrived in Randolph Co., they found the Iowa, Sac, and Fox tribes. Each of these tribes had settled here themselves only shortly before the arrival of the first Randolph Co. pioneers. The first known settler in what is now Randolph County was William Holman along with his father, James Dysart, and brother Joseph Holman. They settled in 1818 near what is now Mount Airy. He was soon followed by Allen Mayo, who settled not far away. James Dysart opened the first school in the settlement that would one day be known as Huntsville in 1822.
Huntsville, the oldest settlement in the county was settled around 1821, and Milton about the same time. At that time, Randolph County was a part of Howard County which extended north to the Iowa border. What is now Randolph County was then made a part of Chariton County to the west. Randolph County was organized out of Chariton County, January 22, 1829, and named in honor of John Randolph, of Roanoke, Virginia. At the time it extended to the Iowa Border. The county seat was located at Huntsville on December 4, 1830. And on the 5th of January 1831, four land owners, William Goggin, Gideon Wright, Daniel Hunt (grandfather of Arizona's first governor George Hunt), and Henry Winburn donated land where the courthouse sits today. As Hunt was the first to settle on the hills of Huntsville, the town was named for him. Previous to that, it had also be known as Gogginsville, as Goggin was the first store owner. General Robert Wilson was the first lawyer in the county and the first circuit clerk (later he would become a United States Senator). Randolph County's first sheriff was Hancock Jackson (later governor of Missouri and cousin of Confederate governor Clairborne Jackson). Its first doctor was William Fort, who also served on the first county court. The other Commissioners on the county court were James Head, and Joseph M. Baker. The first courthouse was completed in the Fall of 1831. It was a two story brick building with one room on the firrst floor used as a courtroom and three above for jury rooms.
The first lot sale took place in April of that year. Huntsville and the county soon prospered with the manufacture of salt, coal mines, hemp rope factories, and tobacco factories. At one time, Huntsville was the second largest leaf tobacco market in the state. By 1857, it was the home to Mount Pleasant College which produced Doctor Victor Clarence Vaughan, one of the finest medical minds of the late 19th and early 20th centuries. The college closed in July,1882 after its main building was destroyed by fire. In 1829, Randolph County saw military action with some Iowa Indians. "Cabins of White Folks" was a very small settlement near what is now Kirksville settled by James Myers, Isaac Gross, Stephen Gross, Nathan Richardson, Reuben Myrtle and Jacob Cupp, all formerly of Howard Co. They had been there about a year when a large body of Iowa Indians lead by Chief Big Neck showed up. One of the Indians' dogs killed a pig, and they threatened the women. Alarmed, they sent messengers south to Randolph County. The messenger reached the home of William Blackwell the night of July 24, 1829. A Captain. William Trammell with a group of men went north to help them, engaged the Indians, and were forced to retreat. Routed, they returned to the cabins, got the women, and headed for Huntsville. John Myers, James Winn, Powell Owensby, and Capt. Trammell were killed in the fight. Later, a force of militia under Gen. John B.Clark lead and two other companies under against Captain Abraham Gooddring and Captain Scounce went after Big Neck. Big Neck and his braves, Big Snake, Young Knight, and One-that-Don't-Care were apprehended March 11, 1830, and put on trial by a grand jury of Randolph County. The jury found on March 31, 1830 that: "After examining all the witnesses, and maturely considering the charges for which these Iowa Indians are now in confement, we find them not guilty, and they are at once discharged." Other than this incident, Huntsville did not see much activity during or prior to the Black Hawk War of 1831 - 1832. Two forts built north of what is now Kirksville, Mo., Ft. Matson and Ft. Clark never saw action. In 1833, in her father's home in Silver Creek, Marsha Head, daughter of Dr. Walker Head was married to Sterling Price. Price, of course would go on to be a commander in the Mexican War, governor of Missouri, and General of the Confederate armies in Missouri during the Civil War.
In 1838, the Potawatomi Indians passed near Huntsville on the Trail of Death. They were being relocated from homes in Michigan and Indiana to Oklahoma. During the Mexican War, Captain Hancock Jackson formed a company of about 100 men and went to what is now Santa Fe, New Mexico. The first country fair was held in the Fall of 1854 at Huntsville. In the winter of 1858, the first courthouse was condemned and tore down. A new one, designed by Henry Austin was built in the Spring of 1860. It was a two story brick building with two towers with a balcony and clock. Lincoln County's current courthouse in Troy is very similar. Other early settlements besides Huntsville included Dark's Prarie in 1829 near what is now Darksville and Eldad Church, and Mount Airy in 1837.
Huntsville and Randolph County were not unaffected by the war. It was the site of one "raid" by its son, "Bloody Bill" Anderson, the execution of Confederates, Charles King, Charles Tillotson, and D. S. Washburn, and the first daylight robbery of a train. On the 28th of August, 1861, Confederate Col. Poindexter held up a train at Old Allen (what is now northern Moberly). There he siezed $100,000 in coin being smuggled out of the state from the Missouri State Bank in Fayette. The money was apparently being stolen by Unionist employees of the bank. The money was then reportedly returned to the bank in Fayette by Poindexter.
While no major battles were faught in the county, there were several skirmishes fought in the county. The most significant was Roan's Tan Yard faught near Silver Creek. The battle took place the 8th of January, 1862 withMaj. W.M.G. Torrence in command of the Union forces and Col. J.A. Poindexter, the Confederate. There were only 91 casualties total (11 Union, 80 Confederate), but the battle ended Confederate usage of Randolph County as a base for recruiting and raiding, A small skirmish was also fought near Renick the 1st of November, 1861 with 14 Union soldiers killed. Another small skirmish took place near Roanoke on the 6th September, 1862, and at Huntsville the 9th of November, 1862. Other skirmishes in the area were: Allen on the 23th of July, 1864, Huntsville on the 14th of July and the 7th of August, and Roanoke on the 10th of September.
Most of these skirmishes were between the guerrilla service of the Confederacy and Union regulars in the area. "Bloody Bill" Anderson returned home on the 14th of July, 1864. His "raid" did not amount to much. Having camped near Ft. Henry Church the day before, Anderson road into town and his men robbed the bank of $45,000. A salesman was killed by Anderson's men for trying to run. The money was returned at Anderson's command, and Huntsville escaped harm for the most part. He then burned the depot at Renick and attacked a Union detachment near Allen. Six Union troops and two horses were killed. On July 23 a squad from the 17th Illinois Cavalry was attacked. After this, he moved north into Shelby County where he burned the bridge over the Salt River, and turned south again. He and his guerillas then moved south again, not to return to Randolph County. It was not long after this he and his men committed the Centralia Massacre in what is thought revenge for the illegal executions of CSA regulars at Huntsville, and Palmyra, Missouri. The same day of the massacre, Anderson engaged the 38th Missouri Infantry, USA under the command of Major A.V.E. Johnson between Centralia and Sturgeon, killing 124 of the 147 troops with barely a loss to his own units.
It should be pointed out, the Confederate "guerrillas" were often local partisans. Reports of Anderson's activities in Randolph County show his attacks to be on railroad facilities and Union troops, rarely the farms of those living here. The Union forces were often from Iowa, Kansas, Michigan, and Illinois. They would burn farms, seize horses, and conscript Southern Sympathizers. Renick and Allen were targets for the Confederate partisans as they laid on the North Missouri Railroad, and the CSA troops had orders to disrupt use of the railroads. Roanoke was in a key position near the Plank Road from Glasgow to Huntsville, and was a convient road for both armies to travel. Huntsville, of course, was the county seat, and home to several Confederate units making it a Union objective (much like the former county seat of Macon County, Bloomington, which was burned to the ground by Union forces for its southern sympathies).