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1st Battle of Boonville #1.jpeg

Second Battle of Boonville Re-enactment

Wayne Lammers Collection

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Adapted from “Discover Cooper County” by Ann Betteridge:

Cooper County suffered a great deal during the Civil War. Her territory was occupied almost constantly by one side or the other, and her citizens were called upon to give to the support to first one side, and then the other. Families and neighbors were divided between sentiments for the North and South. Many of the residents had come from the South and sympathized with the South, but still wanted to stay in the Union. The state was truly divided.

Events Leading to the Civil War

When Missouri decided to become part of the Union, many members of Congress were not enthusiastic about admitting another slave state. In 1821, Congress passed the Missouri Compromise, which allowed Missouri to enter as a slave state and Maine to enter as a free state. This kept the number of free and slave states even. By the time the war was over, much of the County was damaged or in ruins.  Most of the livestock had been “appropriated” by one side or the other to feed the troops, and many homes had been stripped of anything of value.


In 1861, the Southern states began withdrawing from the Union. Missourians held a state convention to decide what they should do. Many of the members including Governor Claiborne F. Jackson, were strongly in favor of the South. However, the state voted to remain in the Union. At that time, most of the people hoped to remain neutral if a war came. War did come and Governor Jackson refused to send troops to fight for the Union.


In April, 1861, Fort Sumter was fired upon. This caused much concern. The people of Cooper County were anxious. Missouri was predominantly a slave state; however, it also had strong northern ties. Since it was one of the so-called “border states,” the divisions of loyalty were greater here than in most places.


Lincoln’s call to arms on April 15th stirred sympathy for the South in Boonville. On April 20th, a large crowd assembled at the Cooper County courthouse. Speeches were made and a secession flag was raised. Perhaps it seemed strange that Missourians passed secession resolutions. Missouri wasn’t a direct supporter of the Confederacy, but it was against Federal intervention in its affairs. The people of Missouri saw Lincoln’s call for troops to crush the “revolutionaries” of the South as a direct threat to their state’s sovereignty.

Governor Jackson was a supporter of states’ rights. He favored secession from the Union. The Governor thought that his state had the right to take Federal supplies that were located in Missouri. Therefore, he established Camp Jackson within a few blocks of the Federal arsenal in St. Louis. Everyone, including General Lyon, commander of the U. S. Army in Missouri, knew what Jackson was doing.  Lyon did not like it one bit, so he surrounded the camp, forced the men assembled there to surrender, and then marched them through the streets of St. Louis. A crowd gathered and shouted protests against Lyon’s actions. Rocks were thrown, shots were fired, and about 30 civilians were killed.


More civilians were killed in other skirmishes in St. Louis. Jackson and Lyon met on June 11, 1861, to discuss what could be done to prevent further fighting in Missouri. Jackson was willing to compromise. However, Lyon insisted on the right to move and station troops of the United States throughout the State, whenever and wherever that might be necessary for the protection of the citizens of the Federal movement, or for the stopping of an invasion. This was totally unacceptable to Jackson, so Lyon stated, “This means war.” Jackson fled back to Jefferson City and called for 50,000 troops to help defend the state against the Federal invasion. He picked Boonville as his point of defense and moved there with General Sterling Price, head of the Missouri State Troops.



Jackson set up Camp Bacon at Boonville. The untrained recruits were mostly farmers with their hunting rifles, out to defend their land against attack. Jackson’s officers were against making a stand at Boonville. They wanted to go further south until their troops could be drilled and trained. Jackson said it was necessary to go ahead as planned.


In St. Louis, Nathaniel Lyon was busy preparing the Federal troops. He believed in trying to surprise the enemy. Lyon took three riverboats and steamed up the Missouri. Early in the morning of June 17, 1861, he landed approximately seven miles east of town near Merna.


Meanwhile, at Boonville, Price was sick from diarrhea, so he left on a steamboat to his home in Chariton County. He left Colonel Marmaduke in command with about 1,500 men who had no experience in fighting. The majority of Lyon’s 500 troops had previous military experience. Lyon had artillery, but Marmaduke’s only available cannon was in Tipton.


Marmaduke stationed his men along a ridge about four miles east of Boonville which blocked the Rocheport road. Lyon came up the river by steamboat from Jefferson City, landed his troops a little upriver from Rocheport, and then marched with his forces up the road to Boonville. The Federal troops advanced for almost three miles. Lyon had Captain Totten shelled the brow of the ridge on which the state troops were stationed and his infantry opened fire with their rifles.


The fighting was thick for a while with several wounded on each side, but soon the training of the Federal troops began to show through, and Marmaduke’s men were forced to retreat across a fence into a field. When the Federals advanced up the hill, the state troops opened fire from the cover of a nearby shed and grove of trees.


After fighting for about half an hour, the state troops were forced to retreat. Lyon’s troops took possession of Camp Bacon where they took the supplies. Five men were killed. Lyon advanced toward Boonville. East of the city limits, at the home of T. W. Nelson, the acting mayor, and several citizens surrendered the city to Lyon.


Marmaduke left for Lexington on a steamboat, and Governor Jackson headed down the Georgetown road. General Parsons of the state militia arrived from Tipton with the state’s artillery after the battle was over. When he found out that the state had lost, he took his command south to Prairie Lick where most of the other state troops were. The next day General Lyon pardoned all of the people who would promise to support the U.S. government and to never again take arms against it. Many people accepted this.


Lyon sent part of his troops to find Jackson, but was unable to locate him. They returned to Boonville. On June 20, three days after the state troops had been defeated, Lyon organized the first Boonville Home Guard, consisting of local citizens. Most of them were of German descent. Their orders were to guard Boonville against invasion by state forces. Similar “home guards” were being organized all over the state. Boonville’s consisted of 135 men with Joseph A. Eppstein elected as captain. Before Lyon left Boonville, he also ordered a small fortress to be built. It consisted mostly of breastworks and a small ammunition bunker which was located on the old state fairgrounds, where St. Joseph Hospital stood for many years.


Eppstein heard rumors that they were going to be attacked by Confederate-sympathizing forces from nearby counties. He ordered several southern sympathizers from the community to be held hostage in the breastworks. The breastworks consisted of a series of poles that had been sharpened at one end and tied at the middle to form a barrier about seven to ten feet in height.


By July 2, 1861, General Lyons had received reinforcements from Iowa and marched out of Boonville to chase the Missouri State Guard under General Price. Price was thought to be collecting troops in southwestern Missouri. With 2,400 troops, the caravan moved along the Boonville-Georgetown Road (the old Spanish Trail to Mexico). They camped the first night at the Clear Creek Crossing. The young Iowans were in woolen uniforms and Private George Ware’s diary complains of the heat and dust. The next day, as they marched past Pleasant Green, young boys hiding behind the orchard wall (the remains of Winston Walker’s old Indian fort) pelted the soldiers with green apples. To their surprise, the soldiers caught most of the apples to save for ripening. At the Lamine River bridge crossing shots were fired at the soldiers from the bluffs, but there were no injuries.


Lyon’s march ended at Wilson’s Creek, near Springfield, where he was killed in battle with the Missouri State Guard. His unburied body was discovered July 13th by members of Kelly’s Regiment (who had been with Marmaduke in the Battle of Boonville) and given proper burial in the garden of John Phelps.



On December 13, 1861, while eating breakfast, Boonville’s Home Guard was attacked by about 800 men from Saline County under the leadership of Colonel Brown.


As rain and musket balls fell, the Confederates advanced twice, but each time they were forced back. Col. Brown was killed in the second attack as was his brother, Capt. Brown. Only two of the Home Guard were killed, but an unknown number of Brown’s men were killed. Major Poindexter took command of the entire force after the death of the Brown brothers. William Burr, a hostage in the breastworks, was given permission to visit the Confederates to see what arrangements could be made to stop the fighting. The two sides agreed on a six-day armistice.


After a week’s armistice, Major Poindexter withdrew his troops to join General Price, who had successfully taken Lexington.



Railroad tracks were laid through Otterville in 1861. In January, 1862, the Sixth Iowa Union Infantry, out of Des Moines, made a march to Otterville and dug the tranches. They camped there most of the winter. Regiments from Illinois, Iowa, Missouri, and Indiana stood in the trenches.

Some of the evidence of the Civil War can still be observed at Otterville. Trenches, which are about six-foot depressions, along with their accompanying breastworks can still be seen on the John Kuykendall farm one mile east of Otterville, south of the railroad tracks.


The original purpose of the trenches was to protect the railroad line going through Otterville from Confederate forces. Union troops stood in the depressions firing over the breastworks at the Confederate soldiers who were attempting to cut the railroad line in half to stop its continued use by the Union to send munitions and supplies to their men in the west.


The railroad ended in Sedalia, where goods were transferred to wagon trains to be taken to Kansas City, Springfield, and other stations. To stop the goods from going through, there was constant fighting and skirmishing up and down the Missouri Pacific Railroad line from Otterville to California. Otterville was more subject to attack because the rail line crossed a trestle over the Lamine River near Otterville. The trestle was burned three times during the war by Confederate soldiers with the help of local citizens.


When James Wear, a current resident of Otterville, was a young boy, he used to play with bullets, belt buckles, and other artifacts from the Civil War found near his home. Other Civil War historians have also found artifacts in the area near the trenches.


Reference: Commemorative Issue, Cooper County Historical Society Dedication of the Historical Marker for the Otterville Civil War Entrenchments October 9, 1999.


General Joseph Shelby, of the Confederate Army, made a raid into Cooper County during October 1863. He passed through Otterville on the night of October 9th, and burned the Pacific railroad bridge nearby. On the night of the 10th he camped near Bell Air, in a pasture belonging to Mr. Nathaniel Leonard. The next day he marched toward Boonville. His movements had become known in Boonville and a meeting of the citizens was called by Mayor McDearmon. After some delay, the conclusion was reached that the only alternative was to surrender the city to General Shelby. Citizens were sent out to meet him. They returned without being able to learn anything about where he was, so they felt that he probably wouldn’t be coming to the city. His arrival at Boonville on October 11th was quite a surprise.


Just as General Shelby marched into Boonville from the south, Major Leonard, with about 150 Federal troops, appeared on the north side of the Missouri River and commenced crossing with his men. When they learned there were many Confederates in town, they decided to retreat. They turned the boat around and headed for the Howard County shore. At this time some of Shelby’s men appeared and commenced firing upon the boat with muskets. As soon as Major Leonard landed his forces, the artillery was turned upon Shelby’s troops and they were forced to retire beyond the reach of the shells.


At the same time, Colonel Crittenden, of the Union, was steaming up the river in a boat. On learning the situation of affairs at Boonville, he dropped down the river and landed a short distance below on the Howard County side of the river.


General Shelby stayed in Boonville the rest of the day, then camped for the night west of the city on the Georgetown road. He had come to Boonville to obtain supplies, such as food and clothing. The local clothing companies lost $4,000 in clothing. The Confederate troops did not hurt anyone during their stay. Not a single citizen was killed or wounded, and they were very polite to everyone.         


While the Confederates were in Boonville, the Federals, under General Brown, were close behind them. On October 11th, the Federals were within eight miles of Boonville, on the Bell Air road. That day General Brown moved a portion of his troops west to the junction of the Sulphur Springs and the Boonville and Georgetown roads, which is about seven miles southwest of Boonville. During the night, he marched his command back again to the Bell Air road, and camped near Billingsville. The next morning after General Shelby had left, the Federals passed through Boonville in pursuit, they advanced just behind the Confederate rear guard. Two of General Shelby’s men stopped at Mr. Labbo’s house, about one and one-half miles west of Boonville to get their breakfast. They were killed by some Federal scouts as the two appeared at the front door to make their escape.


A running fight was kept up at intervals, all along the route from Boonville to Marshall. The fight became pretty heated between the Sulphur Springs and Dug Ford. At Dug Ford, two Federals were killed and fell from their horses into the water.


Theis raid produced great excitement. It is not known whether General Shelby was able to obtain all the supplies and reinforcements that he had hoped. Major Leonard and Colonel Crittenden crossed their commands over the river to Boonville about ten o’clock on the morning of the 12th. After stopping for dinner, they started in the direction of Marshall.


Boonville was then clear of troops. The citizens had time to gather supplies to feed the next group of hungry soldiers who happened to land there, whether they were Federals or Confederates. Thus, ended the famous “Shelby’s Raid” as far as Cooper County was concerned.


A battle took place at Marshall in which a number were killed and wounded on each side. General Shelby succeeded in escaping from his pursuers with the loss of only a small portion of the supplies he had obtained in Boonville.


The first known homeless veteran

(2020) Last Civil War Widow Dies

Helen Jackson, of Marshfield Missouri, was only 17 years old when she married Union veteran James Bolin, 93. He needed care every day and Helen provided that care after she came home from school. Since Mr. Bolin had no money to pay her for her help, he asked her to marry him so that she could have his pension in payment for her care. They were legally married from 1936 to 1939, when Mr. Jackson died. Helen kept her marriage a secret for many years and never applied for Mr. Jackson’s pension. She was an active member of the Daughters of the Union Veterans of the Civil War.


Last American to Collect a Civil War Pension

Irene Triplett, was the (2020) last American to collect a Civil War pension. The fact that someone in the year 2020 was still earning a Civil War pension was the result of two factors: First, she suffered from cognitive impairment, qualifying her for the lifelong pension as a helpless adult child of a veteran. Second, her father, Mose Triplet, who’d served as a private in the Confederate Army before defecting to the Union, was on his second marriage when she was born in 1930, and he was 83 years old. Irene received $73.13 each month and seemed to be very secretive of where the money came from.


Missouri State Archives - Civil War in Missouri 

Also see Veteran Research.

Confederate Veteran Archive. The Confederate Veteran was a magazine published from 1893-1932 and this site has most of them on it. It also has a link to the Sons of Confederate Veterans organization 

Union Civil War Federal veterans, members of the Boonville Camp No. 3701

are lined up on the corner of Main and Spring Streets circa 1900.

From the Wayne Lammers Collection



Stories courtesy of Bert McClary:


Thomas, Abe and the Lieutenant

Late at night in June 1863 Thomas Brownfield, a Union Home Guard Captain, heard noises outside his three-room log cabin south of Pilot Grove, and went to the loft with his gun. A Confederate recruiting agent and several men from New Lebanon were up to no good, looking for firearms. They forced open the door and the leader, Lt. Brownlee, was shot in the doorway. Thomas’ brother Abe pulled him inside and locked the door. The others thought him dead and set fire to the cabin.


Lt. Brownlee shouted to them to put out the fire. Thomas told them he would send for a doctor, would not turn Brownlee over to the authorities, and would release him after he was treated.  They agreed and left, and Thomas kept his word, sending Abe for Dr. Pendleton. However, Thomas did tell a lie, as Brownlee was treated and turned over to the Union militia and placed in the Boonville jail.

Thomas Brownfield is my second great-uncle.Abraham Brownfield is my great-grandfather.


Cynthia and the Notes

Cynthia McClary was home alone southeast of Pilot Grove on the day in 1862 that a group of bushwhackers or militia came to the house and demanded all the livestock. Cynthia had no choice but to comply, however she did manage to chase away one old mare that she knew would return later. She knew one of the men as a neighbor just two farms down the road, and her husband James McClary was shot by the neighbor when he went to inquire about the livestock.


Cynthia was now a 43-year-old mother twice widowed, with three children age ten and under. She could not read or write and owned one old mare.  She had been given “notes” in reparation for the livestock that was taken, presumably a type of government promissory notes. 


Cynthia was probably a southern sympathizer, with Native American and Scots/Virginian heritage. She believed the notes were worthless and she burned them. Cynthia McClary is my 2nd great-grandmother.

The Key and the Crowbar

Mary Carroll was a southern girl living in the Pilot Grove neighborhood of James McClary. Her brother Dennis was arrested and placed in the Boonville Jail along with a Confederate Lt. Brownlee and others. Also in the jail was John Hildebrandt, accused of murdering his neighbor James McClary. Hildebrandt attempted to kill Carroll with a knife, but Carroll broke his hand with a stick of firewood. Mary struck up a friendship with the jailer and surreptitiously made a wax copy of his jail cell key. She made a key of wood and leather and smuggled it, a crowbar, and a bottle of chloroform to Dennis. On the night of the escape Hildebrandt was chloroformed so he could not alert the jailer, and almost died. In the words of Mary, this act “unintentionally came very near being a great benefit to the world.” Hildebrandt was soon acquitted of murder and released, and Dennis was shot and killed. Such was life on the border in 1863. James McClary is my 2nd great-grandfather. 

James McClary and the Bushwhackers

During the Civil War in Missouri renegade bands or individuals from both sides committed atrocities, purporting to represent the Union or the Confederacy. Some individuals used their membership in a group, or the conflict itself, as an excuse or cover to settle personal disagreements.


In September of 1862 a group of bushwhackers or militia took the livestock of James and Cynthia McClary, who lived southeast of Pilot Grove, while James was away. When James returned, Cynthia told him one of the raiders was John Hildebrandt, a neighbor. When James went to confront him, he was shot by Hildebrandt as he approached.


Hildebrandt was held in the Boonville Jail for 18 months, charged with “murder in the first degree”. During that time, he attempted to kill a young southern sympathizer who was also a prisoner. At his trial the jury quickly found Hildebrandt not guilty, the killing of James, from the evidence, appearing to be an act of self-defense on his own premises. Such was life on the border in 1862.

Bloody Bill and Captain Brownfield

In the fall of 1863 when Bloody Bill Anderson’s guerillas approached the country post office outside of Pilot Grove, Captain Thomas Brownfield of the Union Home Guard slipped into the postmaster’s house. The guerillas relieved about 20 local farmers, waiting for the mail, of their valuables. Mr. Mayo refused, was shot in the leg, and ran. Captain Brownfield also ran and they were pursued by guerillas on horseback. Mr. Mayo was shot and killed but Captain Brownfield reached a thicket after being shot in the hand.


He hid in the center of the thicket and fired a warning shot to let them know he was armed. The band of guerillas considered his concealment, then rode away with their loot and their lives. After dark Captain Brownfield made his way to a neighbor’s home, a country physician and friend, although a southerner by birth and sentiment. His friend dressed his wound and fed him, and they slept in the barn as a precaution. James McClary is my 2nd great-grandfather. Thomas Brownfield is my 2nd great-uncle.

Killed by Guerillas

Wilma Bringarth/Bledso talked about her Great-Great Grandfather, Jacob Neef, who was walking back home from Boonville in his Home Guard uniform, during the Civil War, when he was killed by Guerilla's near the Old Lamine Church and was buried in the cemetery there.

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Cooper County Jail – 1858 – In Boonville. Used as a prison for southern sympathizers. Frank James was arraigned here and released on bond.

Concord Cemetery – 1817 – Near Bunceton. One of Quantrill’s men was wounded and secretly cared for by neighbors. Upon his death he was buried in an unmarked grave.

Thespian Hall – 1857 – Originally Stephens Opera House. Building was used as a Union prison and hospital during Union occupation. Main Street, Boonville.

Pleasant Green – 1820 -Located on General Lyon’s 1861 route to Wilson’s Creek Battle. Raided in 1864.

Crestmead – 1859 – Built by John Taylor, a Southern sympathizer who was sent to Gratiot prison and lost his land holdings.

Mt. Nebo Baptist Church – 1856 – Site of General Sanborn’s Union encampment October 1864.

Ravenswood – 1880 – Built by Unionist Leonard and Nelson families after the war for Captain Nathaniel Leonard and his new bride. On route #5 near Bellair.

Markers in Cooper County Tell the Civil War Story

MERNA – where the Missouri River once met the Boonville bluffs, a grey stone marker stands by the railroad tracks. Erected by the Grand Army of the Republic in 1929, it is the landing site of General Nathaniel Lyons and his Union army on June 7, 1861. They had steamed up river from St. Louis to surprise the Missouri Volunteers camped uphill.

DNR MARKER – at encampment located by the Missouri Correctional Center – the story of the morning attack upon the new Missouri State Guard recruits, and the confused fighting that followed is told on a descriptive panel. This is considered to be the first land battle of the Civil War.

PILOT GROVE MARKER at LIONS PARK – Union General Lyons refreshed his forces in Boonville with Iowa recruits and headed southwest from Boonville on the old Georgetown Road in July 1861 to attack the Southern forces gathering at Springfield. Their first night encampment was at the Clear Creek Crossing near Pleasant Green.  Pilot Grove was also the site of a raid by “Bloody Bill” Anderson.

The SECOND BATTLE OF BOONVILLE – This marker by Thespian Hall is where barricades were hastily built when southern sympathizers and the State Guard attempted to regain Boonville for the South. The Union wounded were caried  inside the hall which was being used as a prison for the Confederate captives.

SUNSET HILL CEMETERY – The Union occupation of Boonville was often stormy. Eight Union soldiers were killed in Howard County chasing “Bloody Bill” Anderson and brought back to the City cemetery for burial. A U.S. Government plaque at the mass grave tells the story.

WILKIN’S BRIDGE – During the short occupation of the city by General Shelby and his Confederate forces, many skirmishes occurred out in the county, notably at Wilkins Bridge east of Billingsville on the Billingsville Road. The old covered bridge over the Petite Saline is long gone, but a large flat stone with a bronze plaque erected by the Cooper County Historical Society tells of the violent meeting here of General Sanborn’s Union Army and the Shelby Confederates in October 1864. 

Sanborn’s Union forces moved west from here and the old ante-bellum homes and churches provided campsites, horses food and fodder as the troops moved toward Marshall for the next confrontation with Shelby’s Confederates.

OTTERVILLE – From December 1861 till May 1865, Union troops were stationed around the railroad bridge crossing the Lamine River east of Otterville. There defensive trenches extended nearly a mile. The Missouri Dept. of Natural Resources erected a descriptive marker at the Conservation Area boat launch at the site of the former “Camp Curtis” on Highway A. Regardless of the strong defense, the Confederates managed to burn the bridge three times during the occupation. At the top of the hill there is a flag pole and a small bronze plaque donated by the Cooper County Historical Society indicating a section of the 8’deep trenches on land owned by the David McKinney family.

A Free Map and information for these sites is available at the CCHS Research Center.

Confederate Veteran Archives. The Confederate Veteran was a magazine published from 1893-1932 and this site has most of them on it. 

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