Battle of Round Pond & The Murder of John Chasteen

Round Pond was filled in many years ago and no longer exists but I did find a picture of it in the February 16, 1982 issue of the Southeast Missourian Newspaper

I found this article about the Battle of Round Pond, which occurred in southern Cape Girardeau County, Missouri August 1 , 1863. This article was previously posted on another website that I used to maintain so I though readers of my current website might enjoy. Official records indicate that the battle took place near the Castor River but this is incorrect as the Castor is several miles south of the location and I believe the official reports confused the Castor River with the Whitewater River which is much closer to the location of this event.

This article was orginally published at  

Round Pond Massacre

And the Death of John Burton Chasteen[1]

1 Aug 1863

By Susan Slap-Hoysagk

Setting the stage for Round Pond.

On this particular Saturday in 1863, a Union wagon train of 30 wagons, 20 guards, and 40 teamsters and camp workers had stopped to spend the night on the Bloomfield Road at Round Pond, Missouri.  They were carrying supplies to Brigadier General John Davidson’s troops in Arkansas.  The encampment was attacked in the night by guerrilla fighters called Bushwhackers, who killed and wounded at least 30 men and set afire the wagons. John Burton Chasteen, Sr. charged with aiding and abetting the enemy in the massacre, was arrested by Federal soldiers and taken to nearby Bloomfield where he was held overnight.  John was set free the next morning, found to be innocent at his trial, and started to make his way home.  Somewhere along the way, purportedly about halfway home, he was fatally shot, perceivably in retaliation for bushwhacking.  To fully understand this tragedy requires examining the events leading up to the massacre, including a very torn Missouri during the Civil War, and those after – John Chasteen’s murder left a wife and seven children.

Missouri: Statehood Compromise.

When Louisiana became a state in 1812, the remaining lands of the original Louisiana Purchase of 1803 became the Missouri Territory.  Six years later Missouri requests admittance to the Union as a slave state fueling a national controversy and series of crises as this would upse the balance of equal representation in the Senate between slave states and free states (in essence the issue is of slaveholders having power and control over the national government).  Embittered debates ensued with a compromise of Missouri being admitted as a slave state and Maine as a free state – thus preserving the worrisome balance of Senate representation. Missouri became the 24th state in 1821. The Missouri Compromise did prohibit slavery in the remaining portion of the territory north of 36o30’ parallel except in the state of Missouri.  In 1854 the Kansas-Nebraska Act not only created the territories of Kansas and Nebraska, but also established that popular sovereignty (rule by the people) could decide whether or not to allow slavery, effectively nullifying the Missouri Compromise.  This put another wedge in the nation, splitting it even further and pushing all towards the Civil War.

Missouri Enters into the Civil War.

Missouri was originally settled by slave-owning southerners; however, by 1860 the population had become more diversified with non-slave holding immigrants.  Additionally, the geographical position of the state placed it in the middle of the northern and southern states.  This environment, under pro-Union governor Robert M. Stewart, created Missouri’s decision to try to stay out of the Civil War conflict by remaining in the Union, declaring neutrality, and therefore not giving men or supplies to either side.  Stewart, governor from 1857-1861, was sure Missouri would be destroyed if she seceded.  Claiborne F. Jackson took over as the governor on January 2, 1861, vowing to continue the “armed neutrality” policy of Stewart, even though he favored joining the Confederacy.  On March 21, 1861 at the State Convention, a resolution to not secede from the Union was approved 98 to 1, much to the chagrin of their pro-secessionist governor.

At the top of Jackson’s list of worries was the potential for the St. Louis Arsenal to be used by Union Armies.  This arsenal contained 60,000 muskets, 45 tons of gunpowder, 40 cannons, and 1,500,000 ball cartridges.  Jackson’s fear was realized on Apr 26, 1861 when Federal commander General William Harney’s aide, Captain Nathaniel Lyon, moved nearly to entire arsenal to Springfield, Illinois to prevent the arsenal from falling into Confederate hands in the case of Missouri secession.  Additionally, Jackson had been ordered by President Lincoln to dispatch “four regiments of men for immediate service.”  He refused, responding “Your requisition, in my judgment, is illegal, unconstitutional, and revolutionary in its object, inhuman, and diabolical and cannot be complied with.  Not one man will the State of Missouri furnish to carry on any unholy crusade.

Jackson ordered his state militia to gather for training in the beginning May of 1861, outside of St. Louis at Lindell’s Grove, coined “Camp Jackson.”  He was expecting arms from the Confederate President Jefferson Davis and wanted to secure their safety.  It was also rumored he was preparing to attack and reclaim the arsenal.  Captain Lyon learned of the secret arms being transported and surrounded the camp on May 10th, forcing surrender, which occurred quietly and without violence.  However, a large group of angry citizens had gathered and things at the scene deteriorated very quickly to bloodshed.  People had started throwing dirt clods and rocks at Lyon’s men with some of the civilian men wielding pistols.  One angry drunk opened fire and wounded a Union officer and Union troops started firing into the crowds.  Dead were 28 men, women, and children, with over 100 wounded.  The violence continued for two more days.  On May 11, 1861, a measure is passed by the Missouri General Assembly to create the Missouri State Guard to fight against the Union invasion.  Jackson is removed from office one month later by the recently promoted Brigadier General Lyon[2].  Once predominantly neutral anti-secession, Missourians were polarized into Union or Confederate supporters.  Missouri now has two state governments and the intrastate war has begun.

Lyon and his troops quickly advanced and in June, Governor Jackson was forced to flee Jackson City, the state capital, to Neosho.  In July, with the governor now very much absent, the executive committee of the Missouri State Convention reconvened and declared the existing state offices vacant, appointed the remaining state officers, declared all seats of the legislature vacant, and set a date for the new elections: they also installed Hamilton Gamble as the military/provisional governor.  President Lincoln’s administration then recognized Gamble and his government as the local government of Missouri.  The state now had two governments with Governor Jackson still claiming control.  In Neosho, Missouri, under Jackson, the legislature passed an Ordinance of Secession from the Union the 28th of that October, becoming the 12th state of the Confederacy.  However, this is considered controversial as Jackson’s control over Missouri is in question since Gamble had been declared provisional governor and was recognized by the Federal government as being the legitimate government of Missouri.  The state was claimed by both the Union and the Confederacy, had two governments, and sent representation to governments from both sides.

Missouri’s citizens are now polarized into Union or Confederate supporters, eventually creating a raging civil war with the Civil War, pitting neighbors against neighbors.  Guerrilla warfare broke out and bushwhacking became prevalent in the rural areas of Missouri where sharp divisions between pro-Union and pro-Confederacy abounded.  Most guerrilla attacks or ambushes by bushwhackers were carried out by Confederate citizens and sometimes were on the verge of vigilantism.  Squads of bushwhackers were for the most part organized by groups of young civilian men generally in response to what was considered a Federal invasion of their state.  They took it upon themselves to ambush Federal forces and attack Unionist neighbors and it was not uncommon for bushwhackers to go from house-to-house, executing Unionists.  The government had a very difficult time determining if these were criminal acts or military attacks since the soldiers did not wear uniforms.

John Burton Chasteen, Sr. and Sarah had bought land three to four miles west of Bloomfield, first in 1852 and then added an additional section of 160 acres in 1858.  In 1860, John Burton Chasteen, Sr. is still living there in Castor Township, Stoddard Co, Missouri as enumerated in the Federal Census.  Round Pond, which no longer is in existence as it was drained and filled some years ago, was a little round pond in the western part of Weich Township, in the southern tip of Cape Girardeau Country.  It was southwest of the present-day town of Allenville, then on the Bloomfield Road, the now current County Road 254, and about 26 miles northeast of Bloomfield.  Travelers in those days often stopped there as a rest stop to refresh themselves and their animals.

In The History of Southeast Missouri[3] there is an article about John’s son, John Jr., which does not mention the incident of John Sr. being shot on his way home from Bloomfield after being released in connection with the Round Pond Massacre.  It does not mention military service for John Sr., only which “his sons-in-law and relatives were in the Confederate Army.”  It would seem that John Sr.’s daughter Mary Jane’s husband, Francis Marion Proffer, was a Confederate Soldier.  There is a Francis Marion Proffer, Private, 4th MO Field Artillery, Harris’s Battery, who enlisted in New Madrid Co, (which is just south of Stoddard) on October 1, 1862 at the age of 23[4].  This is certainly the right age as Mary Jane’s husband was born in 1838[5] or 1839[6].  He apparently also participated in Price’s Raid, an 1864 Confederate cavalry raid through the Trans-Mississippi Theater with Major General Sterling Price.  This is the only son-in-law that John had while he was alive as the other daughters were about nine, eight, and three-years-old (Hannah, Martha, and Sarah, respectively).  It would seem logical that John Sr. was pro-Confederacy but to what extent we may never know.

There are limited and varying accounts of what happened that fateful day. Union wagon trains were using this route regularly to carry supplies for General Davidson’s troops.  Southeast Missouri was a hotbed of fighting as controlling the area meant controlling the confluence of the Mississippi and Ohio Rivers.  The following are exerts from The War of the Rebellion, A Compilation of the Official Records of the Union and Confederate Armies.[7] They are reports sent from Brigadier General Clinton B. Fisk. U.S. Army, commanding District of Southeast Missouri and from Colonel John B. Rogers, Second Missouri State Militia Calvary.

Colonel Rogers writes from Cape Girardeau on August 2, 1863, to Brig. Gen. Fisk that “the attack on the train last night was serious,” it was a surprise attack with ten men killed, two mortally wounded, and two slightly wounded.  The train was burned, save three wagons with the mules being recovered but all horses lost.  “There were but 12 of the attacking party.  There must have been inexcusable negligence; but in those swamps the party can approach very near before being seen.”[8]

On August 3, 1863, writing from Pilot Knob, Missouri to Major General John M. Schofield, Fisk states one of General Davidson’s trains of 30 wagons was attacked Saturday night, reiterates the message from Rogers and adds “the entire country along the border is swarming with guerillas…It requires more than half of the force in the district to guard General Davidson’s line of communication and garrison the posts of Bloomfield and Chalk Bluff [Arkansas].”[9] On the same date, Rogers sends another message to Fisk, “The guard was stronger then the attacking party, but the surprise was complete; they were shot in sleep.  It is difficult to guard against such surprise, as the swamp is close to the road and very dense.”  He reports the sergeant in charge of the captured train arrived and he concurred the attack was made from the swamp and “his sentinels on that side were killed instantly and the guerillas rushed on to the half-awakened men and killed them before resistance could be made.  Camping too close to the swamp was the fatal error.”[10]

In his compilation of records is also a correspondence from the Confederate Lieutenant Colonel J. Ellison, Commanding Tenth Missouri Calvary, writing Brig. Gen. J.S. Marmaduke on August 6th from Camp Brown (Union City, TN):

Capt. John McWherter, who has been out scouting on Crowley’s Ridge, has just arrived…Capt John McWherter and 8 other men had an engagement with the enemy at Round Ponds, on the road between Cape Girardeau and Bloomfield, MO. Captain J. [John McWherter] and the others belong to this command. An account of the fight is as follows: The above little party, finding that a train of wagons belonging to the enemy were on the road, followed, and when the guard, numbering 16, also the drivers, were asleep they rushed in on the camp and succeeded in killing and wounding 30.  Destroyed the entire train of 65 wagons by fire.”[11]

Capt John McWherter was associated with the 7th Regiment of the Missouri Calvary (sometimes called the 10th Regiment).  This was organized July 9, 1863 using Kitchen’s Cavalry as the core; its commanders also included the aforementioned Col Jess Ellison.  This unit was also a part of Price’s Missouri Expedition (Price’s Raid).  Listed in the rolls of soldiers for this unit are W. J. Chasteen/Shasteen (Sergeant in Co K.), J.B. Shasteen (Private, Co K and also noted as participating in Price’s Raid; however there is no more information other than his name, rank, and company listed) and a Private John Chastine.

According to these accounts, the ambush at Round Pond was perpetrated by a scouting party of Confederates and not by a group of Bushwhackers.  However, each side had very little tolerance for one another under these hostile conditions of hit-and-run raids and vigilantism, and John Burton Chasteen, Sr. died because of it.

[1] The Round Pond Massacre and the Death of John Burton Chasteen, 1 Aug 1863, By Susan Slap-Hoysagk was extracted from the Jul 07 and Oct 08 copies of the Chestnut Tree, the official organ and publication of The Pierre Chastain Family Association.

[2] Aug 10, 1861, Brig. Gen. Lyon is killed at the Battle of Wilson’s Creek by the Missouri State Guard; some of which were the same men who had surrendered to him just three months prior at Camp Jackson.  He is the first U.S. General to die in the Civil War

[3] Douglas, Robert Sidney (1912), The History of Southeast Missouri (Vol 2).  The Lewis Publishing Co, Chicago and New York.

[4] Confederate Soldiers of Price’s Reid Surnames O through Sh.  Retrieved September 4, 2008 from

[5] 1870 U.S. Census, Bloomfield, Castor Township, Stoddard Co, MO, p.40

[6] 1870 U.S. Census, Bloomfield, Castor Township, Stoddard Co, MO, p.275.

[7] Ainsworth, Brig.Gen Fred C., Kirkley, Joseph W., & Moodey, John S. (1902).  The War of the Rebellion, A Compilation of the Official Records of the Union and Confederate Armies. (Additions and Corrections to Series I, Vol. XXII).  Government Printing Office: Washington.  Pp. 466-468.

[8] Ibid.

[9] Ibid.

[10] Ibid.

[11] Ainsworth, Brig.Gen Fred C., Kirkley, Joseph W., & Moodey, John S. (1902).  The War of the Rebellion, A Compilation of the Official Records of the Union and Confederate Armies. (Additions and Corrections to Series I, Vol. XXII).  Government Printing Office: Washington.  Pp. 466-468.



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