A Body of Wild Riders: The 20th Mississippi Infantry (Mounted)

If you asked most Civil War enthusiast’s what happened in Central Mississippi on May 12, 1863, they would answer without hesitating, “The Battle of Raymond.” They would, of course, be correct, but the Battle of Raymond was not the only fighting that took place that Spring day. Most of these minor engagements were little noted at the time, but they were important to men that fought in them. While doing some research recently I found the following letter published in the Macon Beacon of Noxubee County on July 22, 1863. The missive was written by a soldier in the “Noxubee Riflemen,” Company D, 20th Mississippi Infantry, who only identifies himself as “Bob.”

Although the men of the 20th Mississippi were foot soldiers,  the regiment had been mounted in late April to help run down Colonel Benjamin Grierson’s Union cavalry, which were playing havoc as they raided through the Magnolia State. After General Ulysses S. Grant landed his invasion force at Bruinsburg on May 1, 1863, the 20th Mississippi was ordered to central Mississippi. On May 9, a detachment of the 20th under the command of Lt. Colonel W.N. Brown was ordered to Edwards where they were in position to respond to the movements of the Federal army. They would not have long to wait.

On the night of May 11, General Grant gave his corps commanders their orders for the next day’s march. General James B. McPherson on the Union right was ordered to occupy the town of Raymond. It would be his troops that would fight the Battle of Raymond the next day. General William T. Sherman, in the Union center, was ordered to capture and hold a bridge spanning Fourteenmile Creek near Dillon’s Plantation, some six miles southwest of Raymond.

The Confederate troops defending this bridge were part of a task force commanded by General Wirt Adams. Among the units serving under Adams  was a detachment of the 20th Mississippi commanded by Major Walter A. Rorer. On May 12, while thousands of men were locked in battle at Raymond, just a few miles away a much smaller and more intimate conflict was taking place near Dillon’s Plantation. The following letter is the only account of this action that I have found that was written by a member of the 20th Mississippi. The newspaper that I found it in was faded in places obscuring some of the words, but it is such an interesting letter that I had to share it:


Near Clinton, Miss.,

May 25, 1863

My Dear Father and Mother:

Without knowing exactly how much time I may have to write, will compose a brief narrative of the campaigns of the 20th Mississippi Battalion. I wrote to you from Jackson that, in my opinion, _____ and important events would transpire in a very few days, in fact I _____ battle would occur on Tuesday and Wednesday following which _____ place near Raymond.

Leaving Jackson Monday evening, I reached _____ Depot, where I had previously _____ boys, the same night _____  _____ they had gone out that ______ scouting expedition. _____  _____ until the  next morning __ance of the 20th Mississippi _____ companies) commenced ___is the enemy. Besides _____ there were five or si__ and Col. Wirt Adams _____ two from 4thMiss. cavalry amounting to about 800 men _____ command of Col. Adams.

After going _____ 12 miles from Edwards _____ column halted at a creek _____ and ascertaining the direction the enemy was advancing. Capt. Massey’s company was at the time at Big Black Bridge, two miles further on at Col. Dillon’s farm. Hearing it was about to become engaged pretty soon I hurried on and left the main column and found the Captain busy in felling trees in the road to obstruct the passage of the enemy. About twenty minutes later and a picket comm.___ to report the advance of a heavy body of cavalry. Quickly everything was in readiness, Co. “D” was in line, and awaiting with no little anxiety, the appearance of the foe as the signal to fire. A few minutes later and thick clouds of dust admonished us the approach of the enemy. We had set the bridge on fire to delay their crossing as much as possible. On comes the cavalry, and promptly a murderous volley was poured into their ranks that sent many a riderless horse dashing back. Several men were heard to cry mournfully, but our boys enjoyed the music of their cries, and continued to deal on them their just merits. The cavalry was soon reformed and began to advance again, and another volley from boys again thinned their ranks, and received several shots in exchange.

Map showing the location of Dillon's Plantation
Map showing the location of Dillon’s Plantation

We continued to _____ upon for an hour and a half, when they opened upon us with

Brigadier General Wirt Adams commanded the Confederate troops at Dillon's Plantation
Brigadier General Wirt Adams commanded the Confederate troops at Dillon’s Plantation

artillery and our company was withdrawn to another position. We had them at a decided disadvantage, for we had ___s and fence on them while they were in open view. Gallantly our boys stand to their post and everyone seemed to vie with the other in the accuracy of their fire. To mention the meritorious would be to mention all, but I cannot failed to mention the coolness and gallant conduct of Bo___ Boyle, who was afterwards promoted for his conduct. I was standing by his side behind a fence and watched and admired his coolness. The balance of the 20thMiss. came at a double-quick to our assistance, and after exchanging several shots, fell back by order of Col. Adams. A Lieutenant of a battery stationed at Port Hudson, but acting at that time as aide to Col. A. was with our company _____ in hand, and seemed to enjoy the excitement very much. He complimented all of the company to the Col., but Bob B. was his particular favorite. During this affair Frank with Sergt. Freeman and three more men were about two miles distant acting as picket on another road. They were cut off from us, but joined us the next day.

Col. A’s whole command formed formed line of battle about 14 miles from this bridge in a skirt of woods. He ordered Co. D to take possession of a little house in Col. Dillon’s yard, with orders not to fire upon the Yankee cavalry, but let it pass and to prevent a battery being planted in this yard, was our object. All the boys did not like our position for we would soon have been surrounded and captured without firing a gun, but an “aid” come dashing up and ordered us away, which we obeyed with alacrity.

Finding the enemy too strong for us, the Col. marched us towards Raymond and halted within four miles of the place. He sent me on to Raymond, to report to Gen. Gregg the advance of the enemy in our direction, and also to ascertain the result of the battle at Raymond.

The Battle of Raymond
The Battle of Raymond

I reached the battle field as our men were beginning to retreat and could plainly see our men were outnumbered. Gen. Gregg ordered me to return to Col. A., to tell him to come immediately to his assistance, to protect his rear, but before we could reach Raymond, the Yankees had taken possession of the town, and we had to go through the fields and by a circuitous route to unite with them. After reaching Gen. G’s command we were ordered to Bolton’s and Edwards’ depot. Reaching the latter place, Co. “D” was detached and sent out scouting again, and I was attached to Co. “K” to assist the Capt. Of that company, and in a skirmish that evening, had command of that company. The next morning it was my lot to get into it again; and as we were double-quicking across an old field, a volley was fired at us, but luckily it went above us, and none was hurt. Co. “D” was not present during this skirmish. This skirmish brought on the battle of that day, and which resulted to our disadvantage.

We continued to skirmish with the enemy for three hours, when we retired and then the battle began. We were ordered around to the left, dismounted and marched up and formed line in an old road. On going to the battle field, we met hundreds and hundreds of stragglers, frightened almost out of their senses. On being asked where their regiment was, they invariably replied all killed and captured. These cowardly men had thrown away guns, cartridge-boxes, hats and shoes. I can assure you it was with heart felt pride that I heard the hisses and groans given these men by the boys of the 20th Miss. They called on them to return and go back, but they would not; and so they combined their flight to Edwards’ depot.

I have often spoke in very high terms of our regiment, but I had the only battle of Donelson to warrant me in placing such great confidence in their valor; but their conduct on this battle field, though we were engaged for only two hours, had gained for themselves renewed praise from those who were witnesses. From their conduct at Donelson, I based bright hopes for their future good conduct, and I can safely say my hopes have been more than realized.

Co. “D” was not with these five companies, but was on another part of the field, and was actually engaged. I was still with Co. K, and had two men shot down by my side, while I escaped unhurt. One ball barely missed me, it threw dust on my clothes. Our regiment remained at its post sometime after the other troops by our side had left, and being left alone and unprotected, and having just become exposed to an enfilading fire, we were ordered to retire, which we did with much reluctance, for it was ten fold more dangerous to retreat than to remain where we were, for we had to go across a large high open field. Several were wounded while falling back, only two killed.

Many acts of heroism were displayed some of the officers and especially Major Rorer, who acted with great coolness and deliberation. He appeared as firm and cool as I ever saw him away from the battle. He stood straight up with pistol in hand, walking from one end of the line to the other giving orders &c. All of his men who speak of him, only do so in terms of highest praise and sincerely wish he was Colonel of the regiment.

I heard the 42d Georgia regiment that acted so badly at battle of Edwards and still more disgraceful nearer the depot when a large body of the Yankee cavalry come charging up the road. Major Rorer sent these companies to three companies to their assistance, Co’s K, A, and part of Co. D, under command of Capt. Massey. Already the 42ndGeorgia were thrown into confusion, and Capt. M. called on them to rally, and stand firm. He again called on them to stand, but they could not, and they fled panic stricken from the field. Our men continued to advanced, and the tramping of hundreds of horses close upon us. A few minutes more, and they reached the top of the hill, and we gave them one volley which threw them in disorder, and they retired to form again. We stood there awaiting their approach again, with the determination of driving them back at all hazards, for we knew a great deal depended upon us. Gen. Barton, perceiving us entirely alone, and knowing our inability to defend so large and open a field, had us recalled, when we retired go our horses.

The next day (Sunday) the battle of Big Black bottom was fought, and disastrously to us. We were not present, but were sent down the river to guard the different ferries. On Monday evening Co. “D” Capt. Massey, and a portion of Co. K under my command, were at Baldwin’s ferry, when one of our men, who had been at a house two miles distant, and running in, and reported a large body of Yankee cavalry coming after. They had already captured two of the company, Drew Allen and Hydes with their horses. Capt. Massey and myself with our commands, left immediately that place for the purpose of extricating ourselves. We reached a dense woods in the swamp and halted there, and sent out two scouts to find out where the Yankees were. They returned in three hours and reported them on a road where they expected us to come out at. We retraced our steps and went back the same road we came and reached Vicksburg early next morning.

I have not the paper to spare to give you a full history of our campaign which has been an adventurous one to us. Tuesday we were in the city of Vicksburg when the first day’s battle took place. The bombardment was heavy and lasted till sunset. At 3 p.m. same day Col. Brown received orders to take his command out of Vicksburg, across the enemy’s lines, and report to Gen. Loring, which we did without seeing a single Yankee. We reached Perry depot, on the N.O.J. & G.N. R.R. on Thursday last, and received orders to go beyond Raymond, to hunt all of Gen. Loring’s artillery, which he hid in 14 mile Creek swamp. We halted close to Raymond on Saturday and sent out scouts to see if the artillery was still there, they returned at night and reported it to be gone. So all the mules and horses were sent back to Jackson, and Lt. Col. Brown determined capturing Raymond. We dashed into the place about six o’clock Sunday morning capturing 500 Yankees, about two hundred stand of arms, a few horses &c and many negroes. Two hundred and fifty Yankees were sent to Jackson, the balance being sick and wounded were paroled.

The day before Bob Boyle and John Tyler were sent out as scouts and come suddenly on two Yankees who presented pistols at them and called on them to surrender, but Bob said no, and quickly brought his rifle to bear upon them, when they surrendered themselves. The capture of these two scoundrels proved to be a rich haul. They had 10 or 15 gold and silver watches, a hat full of specie; jewelry of all kinds, Confederate money and Mississippi cotton bills, silver goblets and a host of other valuables, with the names of persons on them. They had eight pistols and one cavalry rifle, which pistols and rifle were given to Bob and John Tyler. Col. B, sent these two men to Jackson, and received orders not to take any more such men prisoners, but to shoot them on the spot.

We received a cordial greeting from the ladies of Raymond. They are nearly scared to death by the negroes. A Yankee gave me a new and valuable blanket. This same man gave three more officers blankets. I did not expect it. They was very kind, and had breakfast ready when we came into town and invited all of us.


Macon Beacon July 22, 1863

The Federal unit that initially made contact with Wirt Adams’ command at Dillon’s was the 4th Iowa Cavalry. In 1893, William F. Scott, Adjutant of the 4th Iowa Cavalry, published a history of the regiment entitled, The Story of a Cavalry Regiment. In this work he describes the fight at Dillon’s Plantation in some detail, and I thought it might be interesting to see how the other side described the fight:

On the 11th Grant’s army was all in hand, prepared for action. The three corps moved steadily northeastward, keeping about parallel with the Big Black River, as if to hold it, but on different roads. McClernand kept to the left, on the road to Edward’s Depot, a point on the Vicksburg and Jackson railway not far from the Big Black; Sherman was in the centre, on the Auburn road; and McPherson on the right, marching toward Raymond.

The Fourth Iowa, in front of Sherman, came upon the enemy at Fourteen-mile Creek,

During the fight at Dillon's, Major Edward F. Winslow narrowly escaped serious injury when his horse was hit and fell on top of him. - THE STORY OF A CAVALRY REGIMENT
During the fight at Dillon’s, Major Edward F. Winslow narrowly escaped serious injury when his horse was hit and fell on top of him. – THE STORY OF A CAVALRY REGIMENT

near Dillon’s plantation, early Tuesday morning, the 12th. The evening before, upon special instructions from Sherman, the Second Battalion of the Fourth Iowa, under Major Winslow, had been sent forward, had crossed the creek by a bridge and examined the country for some distance beyond, but without learning anything of the enemy. Perhaps the bridge should have been held over-night, but it was not so ordered. The enemy occupied the position during the night, and in the morning burned the bridge. Then, concealing themselves in the dense thickets along the northern bank, they awaited the head of Sherman’s column. 

This was the Fourth Iowa, the second battalion being in front. As the advanced company turned a bend of the road and observed the smoking bridge, the enemy opened fire from apparently a long line. The

Flag of the 4th Iowa Cavalry - www.iowahistory.org
Flag of the 4th Iowa Cavalry – http://www.iowahistory.org

whole battalion was immediately thrown into position in the wood on the left of the road, and returned the fire, though without seeing the enemy. The Third Battalion was formed on the right of the road and the First on the left of the Second; and all joined in the fire, but the rebels held their position. As the creek could not be crossed without a bridge, and the position and force of the enemy could not be discovered because of the thick woods and underbrush which concealed them, Sherman ordered up a battery, with infantry in support, and opened the guns at short range. This soon silenced the rebel fire; and the bank of the creek being gained, the bridge was repaired and the corps crossed before noon. It was afterward learned that the enemy was Wirt Adams’ cavalry, a body of wild riders with whom the Fourth Iowa were to become well acquainted in the field.

The fight at Dillon’s Plantation was just a little piece of a much larger campaign, and the casualty reports reflect this. The Confederates suffered only two dead and one wounded; Adjutant Scott wrote that the 4th Iowa Cavalry had one man killed, three wounded, and four horses killed. Little remembered today, the fight at Dillon’s Plantation was one of hundreds of such skirmishes that took place in Mississippi during the 1863 Vicksburg campaign.


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