Battle of Monroe’s Crossroads, Last Large Cavalry Clash of the Civil War

The Battle of Monroe’s Crossroads, sometimes known as the Battle of Fayetteville Road was the last major cavalry engagement of the Civil War. The Union cavalry called it colloquially “Kilpatrick’s Shirttail Skedaddle”.

It took place in what is now northeastern Fort Bragg, NC.  Confederate cavalry under the command of Major General Wade Hampton and MG Joseph Wheeler surprised the Union cavalry of Major Gen. Hugh Judson Kilpatrick early on a rainy, misty morning in March of 1865 and nearly captured the general himself before they were forced back.

But the daring Confederate raid which encompassed over 4500 troops from both sides stopped Kilpatrick from taking the city of Fayetteville, just to the east.

Background: Union general William Tecumseh Sherman had been conducting his famous “March to the Sea” since the previous fall and he knew the end of the war was fast approaching. When setting out on this operation, he was assigned the brave, and often times reckless Kilpatrick as his cavalry commander. Sherman wasn’t a fan of the brash cavalryman but knew that he was tailor made for this operation.

“I know that Kilpatrick is a hell of a damned fool, but I want just that sort of man to command my cavalry on this expedition.”

To his men, whom he frequently subjected to rash charges and reckless and sometimes foolish attacks, he was known as Kilcavalry for Kill Cavalry. But he just as often got results. He delighted in destroying southerner’s property and always operated on the edge. The very cusp between rashness and being court-martialed.

Kilpatrick’s men were approaching Fayetteville while the main wing of the army under Sherman was pushing on Goldsboro, NC. They were planning on pushing thru to Virginia and help General Grant going up against Robert E. Lee outside of Richmond and threaten the rear of his forces.

Kilpatrick stopped for the night at the Monroe farmhouse which was abandoned which was at the intersection of Yadkin and Morganton Roads. The weather was heavy rain on the night of March 9th and the trails were muddy and had slowed everything down to a crawl. Kilpatrick’s men had to dismount and push their wagons thru the quagmire.

And in a terrible oversight, they failed to post pickets to their rear. All the while, Kilpatrick bedded down for the night in the farmhouse, enjoying the company of his mistress, a young southern woman he met in Columbia, SC.

Hampton’s men were much closer than the Union troops believed and Hampton was planning on surprising them with a dawn attack on their camp. Hampton himself had done some of the reconnaissance.

Hampton wasn’t a professional soldier, he was an aristocrat, a moneyed southern farmer who raised his own cavalry troop in South Carolina when the war began.  Assigned to Jeb Stuart’s cavalry, Hampton quickly learned the trade and became a trusted and daring commander in his own right. Stuart described him as “brilliant” at the Battle of Brandy Station. After Stuart was killed at Yellow Tavern in 1864, Hampton was then arguably,  the South’s best cavalry commander.

He hand-picked several troopers whose mission it was to capture Kilpatrick himself. Hampton’s forces were joined by Wheeler’s as well as General Matthew Butler, who had been operating independently. The troops were operating together for the first time.

The Battle Begins: The troops of Wheeler were slow at arriving also due to the muddy roads and they moved into position just before dawn. The plan was simple, encircle the troops of Kilpatrick and hopefully capture the general. They moved silently in the misty rain to within 600 yards of the Union troops.

Hampton gave Wheeler the honor of leading the attack, he stayed back with the reserve brigade. As the Confederate troops mounted their horses nearby for the attack, Kilpatrick appeared at the door of the farmhouse in just a nightshirt.

Fresh from a roll in the hay with his mistress, he wanted to check to see if his horse had been fed. The camp was quiet, a few men lolled about preparing for reveille. The rest of the camp was sleeping. Promptly at 5:30, the Confederates struck, screaming the Rebel yell as they advanced.

The initial assault swept thru the Union camp easily. Wheeler’s men routed the sleeping Billy Yanks and took Kilpatrick’s headquarters while freeing about 130 prisoners. Many of the former prisoners picked up arms and joined the fight. Kilpatrick, still in his nightshirt escaped capture by the narrowest of margins. They also captured the Union artillery.

Confederate Captain Bostick rode up, not recognizing the general, and asked for his whereabouts. Kilpatrick pointed to another soldier galloping away and yelled, “There he goes on that horse!” Bostick and others pursued the trooper while Kilpatrick used that time to jump on the nearest horse and escape.

Wheeler’s troops that were supposed to cut off the escape to the rear were stuck in the swamp and not in position allowing the bulk of the Union cavalry to escape. Wheeler made the decision not to pursue and set about with his men at looting the Union camp.

Once Kilpatrick and his officers realized that they weren’t being pursued, they quickly reorganized their men and hastily counter-attacked. This time it was the Confederates who were caught off guard.

The artillery changed hands two more times as the melee in the camp ensued between the two forces. With the battle raging, Hampton knew that Union infantry would soon be arriving on the scene and ordered his troops to withdraw. And moments later, the Infantry of General J.G. Mitchell and his brigade arrived. Hampton’s timing was impeccable.

Both sides claimed victory. Kilpatrick, widely known for fudging his casualty reports, claimed that he lost 150 prisoners. The Confederates claimed to have taken 500. Hampton’s attack, however, kept Kilpatrick out of Fayetteville until the Confederate infantry were able to withdraw across the Cape Fear River. Then they burned the bridges to slow the Union advance. The Confederate forces then concentrated their men around Bentonville where the last major battle of the Civil War was fought shortly after.

One interesting footnote, was General Grant in a report to Washington stated that in his report from General Sherman, Kilpatrick made no mention of his defeat at Monroe Crossroads where most of his staff were captured.

Having visited the area and Bentonville a few miles away many times while stationed at Ft. Bragg, I came across a print of the battle in 1995 and had it matted and framed. It hangs in my office to this day. As a youngster, I couldn’t read enough about the cavalrymen on both sides and this was one of my favorite prints.

And when the Confederates surrendered in Durham, NC shortly thereafter, Kilpatrick made some comments to the Confederate officers, which is when Hampton mentioned Kilpatrick lighting out in his nightshirt. The men nearly came to blows. Ironically both went into politics. Kilpatrick was an ambassador to Chile and Hampton was the Governor and a Senator from South Carolina.

The area of Monroe Crossroads which is now part of Ft. Bragg became a popular place for the people in the area. A monument was erected in 1921 for the Union troops who were buried after the battle in a mass grave. Later it was learned that the Confederate dead were buried there also. And a Confederate marker was added. In 1996, the US Army put up a monument honoring both sides, “To the American soldiers” that fought there.

The site is in an artillery impact area near Normandy Drop Zone.

Photos: US Archive, author