On the morning of July 6th, the last of the Confederate infantry had crossed over South Mountain at Monterey Pass and were marching toward the Mason Dixon Line in the Cumberland Valley. Following a series of pitched battles and skirmishes, the Confederate wagon trains were resting safely near Williamsport. However, the Confederate army was still spread out, and by July 8th, Confederate General Robert E. Lee needed to buy some time for his army to fully concentrate around Williamsport.
Lee’s wagon train had already been harassed by Kilpatrick’s Union cavalry at Monterey Pass, Lietersburg, as well as Hagerstown since the Fourth of July. After the defeat of a portion of Union General Judson Kilpatrick’s cavalry at Hagerstown on July 6th, 1863, and the Union cavalry withdraw from Williamsport by Union General John Buford’s cavalry the same day, the Union cavalry fell back to Boonsboro, resting in the fields surrounding the town. Fearing a Confederate attack, the Union troopers stayed awake while they were bivouacked. The Union cavalry was ordered to hold Boonsboro and keep the South Mountain gaps open for the advance of Meade’s Army of the Potomac. Union General Alfred Pleasanton felt that Turner’s Gap would become a target of attack by Stuart’s cavalry in order to keep the main infantry of Meade’s Army from crossing South Mountain.
Many cavalrymen stated that it had rained since their arrival in Maryland and were surprised when the morning of July 8th, dawned with rays of sunshine breaking through the clouds. Portions of the Union army were closing in on South Mountain, and would soon be occupying the gaps of the where they had fought the Battle of South Mountain. While the Union army was beginning to close in, Lee still needing his avenue of retreat protected. Anticipating the movement of the Union army, Lee tasked General JEB Stuart to locate the Union cavalry and keep them occupied while the rear of the Confederate army at Hagerstown caught up with the main column in their defensive positions along the Potomac River.
While the Union cavalry rested during the early morning hours, the rain from the previous night made the fertile fields miserable and full of mud. General Buford had his cavalry brigades deployed along the National Road. Colonel Thomas Devin was deployed on the left, while General Wesley Merritt was deployed in the center. To Merritt’s right was Colonel William Gamble’s Brigade. Colonel Gamble was ordered by General Buford to take position about a mile and a half from Boonsboro and deploy to the right of the National Road, on the crest of a ridge.
Gamble deployed dismounted skirmishers in a strip of woods to the front, who were supported by a battery holding the center of the line. Gamble also had several men still mounted. Supporting Buford on the extreme left was General George Custer’s Brigade of General Judson Kilpatrick’s Cavalry Division. Held in reserve, and more toward the center of the line was Colonel Nathaniel Richmond’s Brigade of Kilpatrick’s Division.
General JEB Stuart ordered his command forward from Funkstown. He had with him four brigades of cavalry, Fitzhugh, Jones, Chambliss and Ferguson all trotting along the two main roads that led directly toward Boonsboro. General Fitz Lee’s Brigade was left behind at Williamsport while portions of General Beverly Robertson’s North Carolina Brigade were left on picket duty guarding the approaches to Hagerstown. Colonel Milton Ferguson’s Brigade was ordered to take the Williamsport Road and follow that into Boonsboro, while the rest of Stuart’s cavalry traveled upon the National Road. Leading the advance of Stuart’s cavalry was General William “Grumble” Jones, whose brigade ran into resistance at Beaver Creek. The 6th Virginia Cavalry was the lead element for Jones’ Brigade. The 11th Virginia Cavalry supported the 6th Virginia Cavalry during the opening fight.
As Stuart approached Boonsboro, he ordered Captain William McGregor’s Battery, near the Williamsport Road, to fire upon the dismounted cavalry troops guarding the approach to Boonsboro. Union Lieutenant John Calef’s Battery A, 2nd U.S. Artillery quickly returned fire as he was positioned to the right on the National Road. Gunner George Neese of Chew’s Battery recalled “[The Union] promptly opened on us and returned our fire with a business like energy.” Counter battery fire commenced for several minutes reverberating off of South Mountain. The artillery blasted shell upon Colonel Gamble’s men. Just as Gamble’s men were pulling back along with Calef’s guns, Captain Roger Chew who deployed to the west and north of the National Road began to rain shell upon Gamble’s men, who now seemed to be in a crossfire position.
While the artillery was booming, Stuart sent out skirmishers to attack Buford’s command, and Colonel Ferguson came down the Williamsport Road and hit Buford’s left flank. Colonel Devin, seeing Ferguson’s approach, sent out skirmishers to confront the Confederate troopers. Realizing that he may be outflanked, Buford sent for Kilpatrick to bring his division into the fight. General Custer’s skirmishers were sent out to support Colonel Devin. The 6th Michigan had deployed to the left of the National Road, and a portion of the 7th Michigan sent out skirmishers. The 6th New York under Major Beardsley was in the lead to the left of the Williamsport Road, where they were met with heavy, concentrated artillery fire and were forced to take cover in the woods, unable to make it up the hill where the artillery was posted.
Captain William M. Graham of Battery K, 1st U.S. Artillery deployed his battery on the Williamsport Road. As the battle ensued, the wet and muddy fields caused mounted troopers to fight dismounted, making the cavalry fight as if they were infantry. The artillery was also in a bad situation. Members of the 1st U.S. Battery K recalled that the conditions of the field they were in caused the cannon to sink six inches into the ground, leaving the axles under enormous pressure, causing them to crack. Five of the six guns were taken out of the battle. Fuller’s Battery was completely exhausted and low on ammunition.
On the extreme left was the 6th Michigan Cavalry from Custer’s Brigade. Captain James Kidd recalled, “We had here a good opportunity to test the qualities of the Spencer carbines and, armed as we were, we proved more than a match for any force that was encountered. The firing was very sharp at times, and took on the character of skirmishing, the men taking advantage of every cover that presented itself. The confederates were behind a stone fence, we in a piece of woods along a rail fence, which ran along the edge of the timber. Between was an open field. Several times they attempted to come over the stone wall, and advance on our position, but each time were driven back. Once an officer jumped up on the fence and tried to wave his men forward. A shot from a Spencer brought him headlong to the ground, and after that no one had the temerity to expose himself in that way.”
At approximately 8:00 am in the morning, Captain Ernst A. Denicke and Lieutenant C.F.M. Denicke of the signal corps occupied the ruin of the Washington Monument. And after spending a few hours clearing trees they began to communicate with Buford. Signal flags were wig wagging down to Boonsboro assisting Buford in keeping Stuart’s movements in check. The Washington Monument communicated with Boonsboro through a line of communication that went to a hill in front of Turner’s Gap, and then to Boonsboro itself. The open vista seen from atop Washington Monument gave the signalists an advantage.
By early afternoon, after the Confederate cavalry was reinforced, Colonel Devin was forced to fight a delay action, and the skirmishers, already being engaged for several hours, were running low on ammunition. Back on the National Road, Gamble’s and Merritt’s Brigades had been holding Chambliss’ and Jones’ Brigades for several hours and were in the same position as Devin, running low on ammunition. Merritt was, during this time, being pushed further east toward the edge of Boonsboro as Chambliss’ Brigade continued their advance.
Colonel Nathaniel Richmond’s Brigade received their orders to move upon the National Road and hold a defensive position in the center of the line behind Merritt’s cavalry. Once Richmond arrived, he found that the enemy was posted under the cover of woods and large rocks. Colonel Richmond dismounted and deployed the 18th Pennsylvania Cavalry to advance as quickly as they could, and skirmish with the Confederate cavalry. Colonel Richmond also ordered two guns of Lieutenant Samuel Elder’s Battery E of the 4th US Artillery to deploy and shell the woods. During Elder’s deployment Lieutenant Robert Clarke brought up one gun from Pennington’s Battery, and also deployed, and fired into the woods to drive the Confederate skirmishers out.
The 8th Illinois Cavalry was barely holding on to the extreme right of Buford’s line as they were running out of ammunition, and because of this they were forced to retire into Boonsboro for ammunition. General Kilpatrick, realizing the problem reported to General Alfred Pleasanton, told him that Buford may not have a choice but to retire back toward South Mountain. Kilpatrick also told Pleasanton that they will hold on as long as they can.
While the fighting in Boonsboro continued, Union General Oliver O. Howard, commanding the Eleventh Corps, received an order to march quickly to Turner’s Gap. At about 5:00 pm, General Schurz’s Third Division had executed this march. While positioned at Turner’s Gap, General Schurz received a request for additional support from infantry to march to Boonsboro. General Schurz was sent forward to aid Buford. The Eleventh Corps was positioned upon the western slope South Mountain at Turner’s Gap. The First and Second Divisions and artillery were placed in position to the left of the National Road while the First Corps was located on the right side of the National Road.
After 5:30 pm, Devin’s whole line began to fall back using revolvers in order to keep the Confederates back. As Devin’s men retired some of Kilpatrick’s command entered the fight again. Gamble and Merritt also began to fall back in order to re-supply their cartridge boxes. The Confederate troops were pushing closer to the National Road, but were held in check by artillery posted there.
Around 6:00 pm, Devin “was ordered to advance to the extreme front and right, and support the First Brigade, then rapidly driving the enemy up the turnpike.” Devin formed his line behind the First Brigade in the open fields. Union artillery posted at Turner’s Gap, supported the Union cavalry below when they joined the fight.
Shortly afterwards, Gamble and Merritt reformed their line of battle as Kilpatrick’s Division started to give way. Captain Kidd recalled a special incident that occurred when Kilpatrick’s line gave way. “An officer, dressed in blue, with the regulation cavalry hat, riding a bay horse which had the look of a thoroughbred, rode along in rear of our line with an air of authority, and with perfect coolness said, as he passed from right to left, “General Kilpatrick orders that the line fall back rapidly.” The order was obeyed promptly, though it struck us as strange that such a strong position should be given up without a struggle. We had not been under Kilpatrick long enough to recognize all the members of his staff on sight, and it did not occur to any one at the time to question the fellow’s authority or make him show his credentials. The line left the woods and retreated to a good defensive position on a ridge of high ground facing the woods, the enemy meantime advancing with a yell to the timber we had abandoned. Then it was learned that Kilpatrick had given no such order, but the “staff officer” had disappeared and, when we came to think about it, nobody could describe him very closely. He had seemed to flit along the line, giving the order but stopping nowhere, and leaving no very clear idea as to how he looked. There is but little doubt that he was an audacious confederate, probably one of Stuart’s scouts clothed in federal uniform, who made a thorough tour of inspection of our line, and then, after seeing us fall back, very likely led his own line to the position which he secured by this daring stratagem. The confederates were up to such tricks, and occasionally the yankees were smart enough to give them a Roland for their Oliver.”
After giving way to the Confederates, portions of Custer’s Brigade felt it necessary to regain the loss of ground. Captain Kidd recalled “It was presently necessary to advance and drive the enemy out of the woods, which was done in gallant style, the whole line joining. This time there was no stopping, but the pursuit was kept up for several miles. I can hear gallant Weber’s voice now, as he shouted, “Forward, my men,” and leaping to the front led them in the charge. The Fifth Michigan was to our right, and Colonel Alger who was in command was wounded in the leg and had to leave the field.”
While General Carl Schurz’s Third Infantry Division marched down from Turner’s Gap, the battle continued to rage on in the outskirts of Boonsboro. Buford dismounted Gamble’s Brigade to repulse another Confederate attack. Gamble’s men attempted to retake a hill where two Confederate batteries awaited and hid in silence. To make matters worse, Confederate cavalrymen slipped into a stone barn and proceeded to go to work as sharpshooters. Gamble’s men received additional support by portions of Kilpatrick’s cavalry. The Union cavalry then counterattacked, driving the Confederates back.
This forced the Confederate troops from a series of woods while under the attack of artillery fire. Colonel Gamble later wrote in his after action report: “Kilpatrick’s division was relieved on the left and placed on the right but being unable to dislodge the enemy from the woods I formerly occupied, my brigade was again ordered forward; the battery placed in position under a heavy fire; three-fourths of the brigade dismounted and ordered to drive the enemy out of the woods in front, which was accomplished rapidly under a heavy fire of shell and musketry.”
Lieutenant Alexander C. M. Pennington’s Battery M, 2nd U.S. Artillery was moved and deployed in the Boonsboro Cemetery, its last position during the battle. Hart’s and McGregor’s batteries of Stuart’s Horse Artillery Battalion were receiving heavy fire from Pennington’s new deployment. Returning fire, the cannoneers were throwing shells every which way possible. Then, without any notice, Pennington’s guns were withdrawn from that position. Lieutenant Carle Woodruff of Pennington’s Battery later stated that “Every shot fired that missed something in my battery, hit a marble tombstone in that graveyard, and broken fragments of marble came like hail upon my men.”
Realizing that Devin’s Brigade was about out of ammunition, the 1st Vermont Cavalry of Kilpatrick’s Division was ordered to charge down the pike. They were kept in reserve as the battle entered into the evening phase. Earlier that day Kilpatrick became very upset with the 1st Vermont upon discovering that they carried only forty rounds of ammunition instead of the sixty rounds as ordered. Richmond also deployed the 5th New York Cavalry and the 1st West Virginia Cavalry to pursue the retreating Confederates on the left side of the National Road.
By seven o’clock in the evening, Stuart began to fall back due to his supply of ammunition running low, and seeing the Union infantry take position. At 7:00 pm, the Third Division of Eleventh Corps took position on the National Road northwest of Boosnboro. Leaving Ferguson on the Williamsport Road, Stuart withdrew to Beaver Creek.
Buford chased Stuart to Beaver Creek where the fighting would soon come to an end. As Stuart crossed the bridge, a portion of the 1st North Carolina Cavalry would try to hit Gamble’s men once more. As the Union troopers approached, one Blakely gun of Chew’s Battery fired upon them. As Chew’s Battery fired upon the Union troopers, Stuart mentioned that “Each shot seemed drawn to the flying target with fatal accuracy, until the enemy, driven by the shots of the Blakely and followed by shouts of derision of our cavalry, escaped at full speed over the plain.” Buford gave up the fight and Stuart, along with his brigades, moved toward Funkstown where they encamped for the night. Buford and Kilpatrick moved their division back toward Turner’s Gap and Boonsboro where they encamped for the night, bringing the Battle of Boonsboro to a close.