Grierson’s Cavalry Raid: Knocking the Heart Out of Mississippi

In the early morning hours of April 17, 1863, a bright sun crested the horizon east of La Grange, Tennessee, promising a warm spring day. However, for the men of the 2nd Iowa, 6th Illinois, and 7th Illinois Cavalry Regiments, the dawn also brought intense anticipation. In the preceding days, they had been ordered to prepare to move out, to prepare five days rations, and cull down their equipment. The latter not only included their entire supply train, but they were even told to carry no more than 100 rounds of ammunition per man. It was apparent that, wherever they were headed, that they would be moving quickly and that nothing would be taken that might slow them down. Still, despite whatever apprehension they might feel, these Union troopers were happy to finally leave a long, wet winter in camp behind them. They chatted about where they might be headed and some even broke out in song. Little did they know that they were departing on what would be one the most daring and audacious cavalry raids of the Civil War.

That very morning, their commander, Colonel Benjamin H. Grierson had returned from Memphis with orders to carry out a raid deep into Mississippi. The goal would be to destroy as much as possible of the vital rail lines crossing the state between Jackson and Vicksburg, the Confederate fortress stronghold on the bluffs above the Mississippi River. But, beyond damaging the rail infrastructure, there was a greater goal: to distract General Pemberton in Vicksburg, confuse Southern military authorities across the state, and prevent them from effectively blocking General Ulysses Grant’s bold plan to run the guns defending the river at Vicksburg, march his army south along the opposite bank, and then move them across the river, landing them on firm, dry ground somewhere south of Vicksburg. How, exactly, Grierson was to accomplish all this was left to his discretion—his job was to create as much mayhem in the Confederate rear as possible, then return to the safety of Union lines.

In some ways, General Stephen Hurlbut, commander of XVI Corps, could not have picked an odder candidate for this assignment. Benjamin Grierson was a 35-year old music teacher when Fort Sumter was fired upon. He and his wife, Alice, lived quietly in Jacksonville, Illinois, raising a family of seven children. With the onset of the war, Grierson volunteered to be an aide-de-camp to General Benjamin Prentiss, who was forming volunteer units across the state. Soon, however, Grierson, who had been kicked by a horse at age eight and harbored a deep fear of the animals, found himself assigned to the 6th Illinois Cavalry. Somehow, he managed to overcome his childhood phobia and proved a reliable and resourceful cavalry commander while fighting guerrillas in west Tennessee, attracting the notice of General William Sherman, who had recommended him for promotion to colonel and command of his regiment. Sherman said that Grierson was “the best cavalry commander I have yet had.” Grierson’s most notable attributes seem to have been his toughness combined with a quiet, modest, and unassuming demeanor that earned him the respect of men under his command.

Now, 1,700 Union cavalry troopers from the 6th and 7th Illinois Cavalry along with the 2nd Iowa Cavalry, led by a former music teacher who feared horses, would descend deep into the Confederacy. Their mission would require that they maintain a delicate balance between causing enough harm to create fear and confusion in the enemy’s ranks, while confusing him sufficiently to not get caught in the process. Had those troopers known that their commander had only a vague notion of how he was going to do this, they might not have been quite so happy to see La Grange disappear behind them. Grierson had orders only to disable the section of the railroad that ran east from Jackson to an intersection with the Mobile & Ohio Railroad near Newton Station. Beyond that, what he did with his command and, most importantly, how he got back to safety was up to him. As the column left La Grange that morning, Grierson’s only tools were a small pocket compass and a map of Mississippi, and his sole source of intelligence was a written description of the countryside. Everything else would be discovered as the column moved south and Grierson would have to improvise, using his best judgment and ingenuity.

The first 48 hours of the raid was marked my torrential downpours, causing the Mississippi roads to turn into quagmires. Despite this, Grierson’s men still managed to travel 30 miles per day. Thus far, they had encountered a scattered home guard picket or two, but nothing substantial in terms of resistance. On the morning of April 19, Grierson heard that Confederate cavalry might be forming to the east near Chesterville and also in the vicinity of New Albany and King’s Bridge. As Colonel Hatch’s 2nd Iowa had been paralleling Grierson and the main column to the east, he sent word for the Iowans to make a demonstration toward Chesterville. At the same time, he dispatched a detachment from his own regiment to New Albany, and another northwest toward King's Bridge. His goal was twofold; first, to make Confederate authorities aware that his troopers were in the area and, second, to create the impression that his goal was merely to break up these groups of Confederate cavalry.

The expedition to New Albany came upon 200 Confederate troops near the town, and engaged them, killing and wounding several. Meanwhile, the one moving northwest to King’s Bridge found that Southern cavalry under a Major Chalmers had suddenly fled westward in the night upon hearing Grierson’s troopers were nearby. Once his detachments were back in the fold, including the 2nd Iowa, which now rejoined the main column, Grierson moved south to Pontotoc, arriving around 5:00 p.m. As his skirmishers dashed into the town, they encountered minor resistance, killing one militia member and wounding and capturing several others. Once the town was secure, Grierson ordered his men to destroy a large mill, including 400 bushels of salt and camp equipment. Once this task was complete, the column moved forward and encamped for the night on the Daggett plantation, five miles south of Pontotoc.

During the evening, Grierson met with his staff and informed them that he was taking additional action in the morning to further confuse the enemy as to his intensions. First, he detached 175 men from the 2nd Iowa, along with one piece of artillery, all prisoners, led horses, and captured property, and ordered them back to La Grange, marching in column of fours, before daylight, through Pontotoc, thus leaving the impression that the whole command had returned to Tennessee. At the same time, he told Major Love, who commanded the small detachment, to send one scout off and have him cut the telegraph lines to Oxford.

With Love’s detachment safely off to La Grange, Grierson ordered the rest of his force onto the road toward Houston, Mississippi at 5:00 a.m. They would travel without event, passing through Houston at 4:00 p.m., and encamping after dark on April 21. Once again, Grierson made plans to divide his force and, thereby, further confuse the Confederate forces, which were closer than Grierson realized. As he made his plans, a Confederate cavalry detachment under Lieutenant Colonel C.R. Barteau was closing in. They had entered Pontotoc well behind Grierson on the morning of April 20, but soon closed the gap. By daybreak on April 21, they were only a few hours behind the Union troopers. While Grierson was unaware of Barteau, logic told him that, by now, there might very well be someone in pursuit of the main column. Therefore, he ordered Colonel Hatch to leave the main column the next morning with the remaining 500 men of the 2nd Iowa plus one artillery piece. Hatch was to proceed to the Mobile & Ohio Railroad near West Point, Mississippi, destroy the railroad and wires; then move south, destroying the railroad and all Confederate government property as far south as Macon. Once at Macon, he was then to find his way north back to La Grange by the most practical route.

The next morning, Grierson’s column moved out at 6:00 a.m. and, two hours later, upon reaching the road leading southeast, Hatch’s command turned off towards West Point. As he detached from Grierson, Hatch ordered one company and his sole artillery piece to trail the main column for three miles toward Starkville. Once there, the Iowans wheeled about and returned in columns of fours, obliterating the hoof prints left by Grierson’s force. They even turned their cannon about at four different places, leaving distinct sets of wheel impressions, suggesting that four different cannon had turned. If this little ruse worked, Barteau and his men would think that the entire column had turned eastward toward the Mobile & Ohio.

In fact, the ruse did work as planned and Hatch’s diversion worked flawlessly. Barteau, arrived at the junction shortly before noon, and, seeing the hoof prints and tracks, headed eastward in pursuit. Shortly thereafter, as Hatch approached the town of Palo Alto, Barteau attacked him from rear and on each flank, and blocked the road to West Point with an Alabama regiment supported by artillery.

In the attack made by the enemy, a company in the rear was cut off and nearly all taken. The enemy then closed in on my flanks, and advanced in two lines on my rear, with two flags of truce flying, enabling him to approach very close, my command being at that time in a lane, with high fences and hedges upon either side, my men dismounted and well covered. Changing my front to the rear, I waited until the enemy were close upon me, and opened with my rifles and one 2-pounder from the front and with carbines on the flanks, breaking his lines and driving him back, pushing the enemy about 3 miles, capturing arms and horses, and retaking the company lost in the first attack. From that time until dark it was a constant skirmish, the enemy having taken me for the main column. Believing it was important to divert the enemy's cavalry from Colonel Grierson, I moved slowly northward, fighting by the rear, crossing the Houlka River, and drawing their forces immediately in my rear.

As Hatch was fighting off Barteau, Grierson journeyed southward along the road to Starkville with the remainder of his command, now numbering about 950 men. After destroying mail and government property in Starkville, they turned on the road to Louisville, Mississippi. This led the Union troopers through a dismal swamp almost belly-deep in mud and, at several points, the men were forced to swim their horses across deep, murky streams. At noon that day, Grierson dispatched a small group of troopers ahead of the column. In his official report, Grierson called these men “scouts.” But, they were a little more than that. Each of these scouts would replace their Union uniforms with “liberated” civilian clothing. Each would ride ahead carrying a shotgun or long rifle, looking to all the world like a group of hunters. This unit became known as the “Butternut Guerillas” and was the brainchild of Lieutenant Colonel William D. Blackburn of the 7th Illinois. Commanded by Quartermaster Sergeant Richard W. Surby, these men would serve as Grierson’s eyes and ears as they moved further south.

On April 22, Grierson resumed his march towards Louisville, some 28 miles ahead. Once again, his men faced a day of riding through dense swamp, this time along the Noxubee River bottom. The water here was up to their mounts bellies and, as a result, the Union cavalrymen could not even make out the roadway. Despite these challenges, the column made good time and arrived in Louisville soon after dark. Grierson ordered a battalion of the 6th Illinois to enter ahead of the main body to picket the town and remain until the column had passed, when they were relieved by another battalion from the 7th Illinois, who were ordered to remain for an hour. The goal of this effort was to prevent anyone from leaving with information on which way the column was headed and also to quiet the fears of the people. They had heard the Union cavalry was coming and many had fled, taking only what they could hurriedly move. Grierson’s column moved quietly through the town without halting, and his men were careful not to cause any disturbance. Grierson wrote in his final report that, “Those who remained at home acknowledged that they were surprised. They had expected to be robbed, outraged, and have their houses burned. On the contrary, they were protected in their persons and property.”

As April 23 dawned, Grierson was edging closer to his original target: the railroad at Newton Station, Mississippi. He pushed his men forward all through the day and halted to rest and feed the horses until around 10:00 p.m. that evening Then, he dispatched Lieutenant Colonel Blackburn and two battalions of the 7th Illinois towards Newton Station, with the rest of the column following an hour behind. Blackburn, of course, was preceded by the Butternut Guerillas, who arrived at the rail junction just before dawn. The scouts learned a train was expected soon, and, within minutes, they heard the shrieking whistle of a westbound freight train. At the same time, Blackburn and his men had arrived, concealing themselves behind the depot buildings just as a 25-car freight train pulled into the station. As the locomotive drew abreast of the depot, Blackburn’s men leaped into cab, pistols drawn, ordering the surprised engineer to stop the train.

They quickly pulled the train off the main track and discovered yet another train was inbound to the station. Using the same tactics, they seized the second locomotive, which was pulling 13 cars filled with weapons, ammunition, and supplies. An additional car held passengers fleeing Vicksburg with their furniture and other personal belongings. Blackburn’s men removed both passengers and the private property, then gleefully set fire to the train. When the flames reached the ammunition cars, the train exploded with great fury. Five miles away, Grierson heard the explosions and feared a fight was under way. He moved the column forward at a gallop, but was soon relieved to discover that what he had heard was just destruction of enemy ammunition.

Grierson now set about destroying as much rolling stock and track as possible. Both locomotives were blown up, track was pulled up, and a bridge west of the depot was also destroyed. Now, having damaged as much as possible of the railroad in and around Newton Station, Grierson led his exhausted command south about four miles, then stopped. They had been riding for almost 48 hours straight and it was time to rest, if only briefly. As his men took a much needed break, Grierson began to contemplate his next move. He had completed the material portion of his mission, but he now had to continue to create some mayhem, while figuring out how best to get his men back to Union lines. As he later reported,

From captured mails and information obtained by my scouts, I knew that large forces had been sent out to intercept our return, and having instructions from Major-General Hurlbut and Brigadier-General Smith to move in any direction from this point which, in my judgment, would be best for the safety of my command and the success of the expedition, I at once decided to move south, in order to secure the necessary rest and food for men and horses, and then return to La Grange through Alabama, or make for Baton Rouge, as I might hereafter deem best.

After only three hours rest, he ordered his weary men to remount and move out. Upon reaching Garlandville, they found the local populace armed and organized to resist them. The citizens of the town opened fire, wounding one trooper. The Union column charged and captured several of the would-be defenders, some of whom were quite elderly. Rather than being harsh, Grierson lectured them and quickly released them to their homes. Expressing surprise at this benevolent treatment, one man “volunteered his services as guide, and upon leaving us declared that hereafter his prayers should be for the Union Army.”

Grierson then continued south, slowing his rate of march and taking rest whenever he could. By this time, his activities had created a state of alarm across Mississippi, and confusion reigned supreme. Telegrams sent among generals Pemberton, Loring, Buckner, and Johnston indicated conflicting stories of disaster and phantom columns of Union cavalry were reported everywhere, going in every possible direction.

To add to the mix, Grierson decided to send a single scout, Samuel Nelson, to “proceed northward to the line of the Southern Railroad, cut the telegraph, and, if possible, fire a bridge or trestle-work.” Nelson left about midnight, and soon came upon a Confederate cavalry regiment searching for the Union column. Using a slight stutter in his speech, he convinced the Southern commander that he had been forced to serve as a guide for Grierson and, having escaped, would gladly tell them where to find the dreaded Yankees. Nelson then spun a tale, informing them that Grierson’s force totaled over 1,800 men, who were now heading east towards the Mobile & Ohio Railroad. The Confederates thanked him, mounted up, and dashed off to the east in headlong pursuit.

During the night, Grierson learned from other scouts that all his potential routes of escape east and north were effectively blocked by reinforcements of both infantry and cavalry. Therefore, knowing that General Grant might very well be moving his troops across the Mississippi near Port Gibson, he decided to make a rapid march, crossing the Pearl River to strike the New Orleans, Jackson & Great Northern Railroad at Hazlehurst. Then, after destroying as much of the railroad as possible, he would get his small force on the enemy flank and harass them as much as possible.

After getting a full night’s rest, Grierson’s column began its march to the Pearl River on April 26. As they neared the crossing, two battalions of the 7th Illinois galloped ahead to secure the ferry and landing. They arrived just in time to capture a Confederate courier who had come to warn of the approaching Federal column and order the destruction of the ferry across the river. With the crossing captured, Grierson’s men were able to ferry and swim their horses across by mid-afternoon.

As the column crossed the Pearl, Grierson sent his two advance battalions toward Hazelhurst, with the Butternut Guerillas in the lead. Just outside Hazelhurst, Colonel Prince, the commander of the small advance force, handed the scouts a forged dispatch addressed to General Pemberton in Vicksburg, informing him that the Yankees had advanced to Pearl River and, having discovered the ferry destroyed, they could not cross and had turned to the northeast. With all the apparently considerable theatrical skills they could muster, two of Grierson’s scouts rode into Hazelhurst, walked up to a small group of Confederate officers at the train depot, and calmly handed them the dispatch. The officers thanked them, then gave the message to the telegraph operator, who promptly typed the misleading telegram and sent it racing across the wires to Confederate headquarters.

As soon as Colonel Prince returned, Grierson sent him to strike the New Orleans, Jackson & Great Northern Railroad at Hazlehurst. Galloping into town, Prince’s men found a number of cars containing about 500 loaded artillery shells and a large quantity of commissary and quartermaster's stores, intended for Grand Gulf and Port Gibson. They set fire to these and destroyed as much of the railroad and telegraph as possible.

When Pemberton heard that Grierson was in Hazelhurst, he sprung into action, sending everything he had to intercept the Union column. Pemberton feared that Grierson would now swing back to the northwest in an attempt to disrupt communications between Jackson and Vicksburg. Not knowing which way the wily Grierson might go, however, he spread his forces thinly, trying to cover every possible route and every conceivable target.

With the Confederates now gaining on him, Grierson broke camp at 6:00 a.m. on April 28 and he sent a detachment forward to destroy the rail lines at Bahala, Mississippi. When the detachment returned the next morning, they told him that scouts had learned Grierson was riding into a trap set by Colonel Wirt Adams’ Confederate cavalry between Union Church and Fayette, a few miles ahead. Unable to turn back, Grierson decided to boldly spring the trap, and then change direction.

Early on the morning of April 29, Grierson galloped directly into Adams’ ambush, setting it off. However, just as Adams attacked, the main Union column veered sharply from its westward course toward the Mississippi River and headed southeast toward Brookhaven, leaving behind a company to fight a rear guard action. After waiting several hours for the anticipated arrival of the main Federal body, Adams realized he had been duped. He sent a dispatch to Pemberton informing the general that he would now attempt to intercept the Grierson’s new route of march.

After destroying a conscript’s camp in Brookhaven, Grierson’s men moved south along the railroad, destroying all the bridges and trestles along the way. At Bogue Chitto Station, they burned the depot and 15 freight cars, and “captured a very large secession flag.” From there, they continued south, destroying more bridges and freight cars, and adding water tanks to the list of destruction.

Now, Grierson and his men could hear Admiral Porter’s guns bombarding Grand Gulf in the distance, but, with Wirt Adam’s cavalry between him and the river, Grierson decided to head south to Union lines at Baton Rouge. Moving southwest and away from the rail line, Grierson headed for Baton Rouge. That night, his column camped 15 miles southwest of Summit, Mississippi. As they rested, Confederate cavalry continued to close in. One unit had been following the path of destruction Grierson had left behind him, reaching Summit at 3:00 a.m. on May 1, a mere nine hours behind the Federal cavalry. However, Grierson had carefully planted a rumor that he was headed for Magnolia and Osyka, the next stations on the rail line. Hearing that news, the eager Confederates pressed southward in the hope of falling upon the Union column’s rear.

After a few hours of sleep, Grierson roused his men and, initially, they left the road and made a feint towards Magnolia and Osyka, seeming to confirm the rumor he had spread in Summit. Instead, however, Grierson then veered due south, marching through dense woods, narrow country lanes, and, finally, back on the main road. Unbeknownst to Grierson, more Confederate cavalry was trying to close the door ahead of him. Adam’s cavalry was only five miles away and Lieutenant Colonel George Gantt’s 9th Tennessee Cavalry Battalion, which had been chasing rumors of Grierson’s whereabouts for days, had deployed near Osyka, covering the roads to Liberty and Clinton right ahead of Grierson.

As Grierson approached the bridge over the Tickfaw River, his scouts reported that the 9th Tennessee was blocking the crossing. Grierson had no choice but to engage the enemy and, after deploying his artillery, his column charged the bridge. The first two charges were pushed back by withering rifle fire from the Confederates, so Grierson had two companies dismount and pin the enemy cavalry down with rifle fire of their own. Then, he had his artillery blast the woods where the Confederates were positioned with shot and canister, quickly silencing the opposition. As the Tennessee cavalry abandoned the bridge to Grierson, the Federals had only two obstacles ahead, the Amite and Comite Rivers.

Both of these rivers were crossed without major incident, but Grierson was now pushing his men hard to reach Baton Rouge. Many troopers were falling asleep in their saddles and Grierson and his officers worked hard to keep men awake and moving forward. Finally, on the afternoon of May 2, Grierson’s column would finally reach Baton Rouge, where they were given a hero’s welcome. They had traveled over 600 miles in less than 16 days, covering over 76 miles in the final 28 hours without food or rest. During the raid, Grierson inflicted about 100 casualties, while losing three killed and seven wounded. His men had destroyed “between 50 and 60 miles of railroad and telegraph, captured and destroyed over 3,000 stand of arms, and other army stores and Government property to an immense amount.”

Most importantly, however, Grierson had spread panic and confusion in the Confederate rear as Grant made his successful crossing of the Mississippi. And, perhaps just as important, Grierson’s raid severely depressed Confederate morale. Parts of Mississippi were already somewhat Unionist in sentiment and Grierson’s raid, along with Grant’s invasion of the state, heightened popular distrust of Confederate authority. Upon hearing from a Unionist informant about the progress of Grierson’s column, Grant wrote to General Halleck saying,

He has spread excitement throughout the State, destroyed railroads, trestle works, bridges, burning locomotives & rolling stock taking prisoners destroying stores of all kinds. To use the expression of my informant “Grierson has knocked the heart out of the State.”