The twenty-four hour period from the start of the Battle of Monterey Pass on July 4th, 1863 to the finish of the skirmish at Smithsburg on the evening of July 5th, proved to be a very important period for the Confederate Retreat from Gettysburg. Kilpatrick even though was unable to get in front the retreating wagon trains that were moving to Hagerstown, or block Monterey Pass, an important mountain gap upon South Mountain, or hold Smithsburg once Stuart’s cavalry appeared from Raven Rock Pass on South Mountain did capture a great quantity of Confederate prisoners and many wagons. As Kilpatrick left the battlefield at Smithsburg, he took to the roads that followed along the western base of South Mountain and managed to enter Boonsboro around midnight.
Early in the morning of July 6th, General Kilpatrick sent his spoils that his cavalry division had captured at Monterey Pass through Turner’s Gap to Frederick, Maryland where General William French had his headquarter. During the three-day Battle of Gettysburg, the old South Mountain battlefield was occupied by the Middle Department. During the morning General Kilpatrick had learned of the Confederate wagon train that was passing through Hagerstown and he wanted to add to the spoils of what he had already captured.
Around nine in the morning, Kilpatrick had set off toward Hagerstown. As Kilpatrick was pulling out of Boonsboro, he learned of the approach of General John Buford’s Cavalry Division who was at Middletown. Kilpatrick who wanted the support of Buford held off any attacks once his cavalry was closing in on Funkstown. Buford had sent a courier to Kilpatrick telling him about his plan to attack the Confederate wagons that were moving from Hagerstown to Williamsport. Kilpatrick went back to personally talk to him about the situation that was unfolding. While Kilpatrick was heading back to Boonsboro, Buford was already notified of Kilpatrick’s where about. Kilpatrick had sent couriers out and General William French’s command at South Mountain told the general about Kilpatrick’s plan.
During their meeting in the afternoon, Buford and Kilpatrick came up with their battle plans. The plan now called for Buford’s cavalry division to be supported by General George Custer’s cavalry brigade that attack Williamsport as well as protect Richmond’s left flank as he went to Hagerstown. Kilpatrick would personally ride with Buford’s cavalry. Colonel Pennock Huey’s Brigade would travel on a parallel road west of the National Pike and be held in reserve since his brigade was worn out. Colonel Nathaniel Richmond and his cavalry brigade would attack the Confederates in Hagerstown. Leading Colonel Richmond’s brigade was a squadron of the 18th Pennsylvania Cavalry with Lieutenant Colonel William Brinton leading and Captains William Lindsey and Ulrich Dahlgren. Supporting Richmond’s brigade was Elder’s Battery.
After the close of the Battles of Monterey Pass and Smithsburg, he Confederate cavalry was General JEB Stuart’s Cavalry Division was starting to concentrate around Lietersburg. Stuart had under his immediate command two brigades of cavalry, Colonel Milton Ferguson who was now commanding Jenkins’ Brigade due to the wounding of General Albert Jenkins at Gettysburg and the other brigade was under the command of Colonel John Chambliss. As Stuart approached Leitersburg, he was united with portions of General William Jones’ Brigade and General Beverly Robertson’s Brigade that had survived the Battle of Monterey Pass. Stuart also learned of General John Imboden and his brigade that was positioned at Williamsport guarding the wagon train of wounded and supplies. Receiving conformation of Kilpatrick’s retreat from Smithsburg to Boonsboro, General Stuart realized that he needed to keep his cavalry between Lee’s quartermaster wagons and the Union cavalry and to keep Hagerstown and Williamsport secured for the remainder of Lee’s army that was still in Pennsylvania.
Stuart rode to Cavetown via Smithsburg where he issued orders to his brigade commanders as to where they will be picketing and what roads they will be protecting. General Jones was to take his brigade toward Boonsboro and then occupy Funkstown. Colonel Chambliss and Robertson’s brigades were to proceed from Leitersburg to Hagerstown with Chambliss in the lead. As Stuart and Ferguson rode with Jones’ column, Stuart with Ferguson diverted and rode toward Chewsville.
An interesting story that deals with Company D of the 11th Virginia Cavalry takes place prior to the Battle of Hagerstown that is worthy to mention. Nearing Hagerstown, Captain Edward McDonald heard cheering coming from the men. As he rode ahead, he saw the men cheering a 14 year old girl who was wearing an apron that resembled a Confederate flag. Captain McDonald thanked the little girl for cheering his men and asked if he could have a piece of apron for a souvenir. She took of the apron and handed it to Captain McDonald. He then told the girl that as long as his company was on Maryland soil, he would honor her by using it as his company colors. Private James Watkins’ volunteered to carry the honorable flag and returned to his company.
As Colonel Chambliss’ brigade was put in motion, the 9th Virginia Cavalry under the command of Colonel Richard Beale was ordered ahead of the columns to Hagerstown. Upon arrival the 9th Virginia Cavalry did not see any Union cavalry in possession of Hagerstown. Picket’s were thrown south of Hagerstown and still no site of the enemy. That information was sent back to Colonel Chambliss. As the 9th Virginia Cavalry was securing Hagerstown by throwing out pickets, it was seen in the distance that an enemy force was coming. Couriers were again sent back to Colonel Chambliss with the updated status. All roads leading from Hagerstown to Boonsboro, Funkstown, Sharpsburg and Williamsport were guarded. Many of Beale’s men took refuge behind stonewalls and buildings commanding the hill near the Female Seminary and south of the Hager’s Mill. By this time portions of Chambliss’ brigade came into Hagerstown and placed barricades in the streets for the pending attack.
As the 18th Pennsylvania Cavalry approached the Hager Mill, the National Road intersects with Baltimore Street and becomes Mulberry Street. As Chambliss’ brigade was being placed into position, Colonel Beale was instructed “To tole the enemy in.” As the Union cavalry approached, portions of Company A, 18th Pennsylvania cavalry along with one squadron of Major Charles Capehart’s 1st West Virginia cavalry was ordered down one block to Potomac Street. The 9th Virginia Cavalry picketing the road leading to the seminary was quickly overrun and Beale began to loose ground.
Among the Confederate cavalry units was that of the 1st Maryland, Company A under the command of Captain Frank A. Bond. Many of the Marylanders took time to try and locate food not only for themselves, but their horses as well. Captain Bond before he could even finish his meal learned of the Union cavalry threat coming in from the south. Captain Bond managed to get about half of his company mounted and headed back into Hagerstown where he met the advance of Ewell’s wagon train that was under guard of the 10th Virginia Cavalry under the command of Colonel James L. Davis. Colonel Davis had just sat down when the alarm was sounded. The wagons were ordered to halt as the battle was about to take place.
As the Union troopers approached Davis’ barricades, Beale’s men were intermixed with the blue columns. As Davis’ troops prepared for the onslaught their line ran north to south along the main street that Beale’s men were retreating on. Captain Bond had scouted the Union cavalry and reported that information to Colonel Davis. Captain Bond wanted to charge the enemy, but Davis disagreed. Colonel Davis had already established a makeshift barricade on Potomac Street near Saint Johns Evangelical Lutheran Church. Seeing the mass columns charging, Colonel Davis had a change of heart and ordered a charge, he spurred his horse forward when it was shot down and according to Colonel Beale, Davis was seen defending himself with his saber and was captured. Behind Davis’ 10th Virginia Cavalry was that of Captain Bond’s company of the 1st Maryland Cavalry.
Sabers were used rather freely and the Union cavalrymen within minutes pushed further and further up Potomac Street. As the 9th and 10th Virginia Cavalry regiments fled, Captain Bond Marylanders would pull back and quickly come out and hit the charging Union cavalry. During the fight Captain Lindsey was hit and later Captain Dahlgren was hit in the foot. As the Union cavalrymen kept up their rate of speed, Robertson’s Brigade and Chambliss’ Brigade formed up and upon seeing the Union troopers, fired on them.
As the battle was in full swing, couriers had been sent out to General Stuart. Stuart hurried with Ferguson’s Brigade to Hagerstown coming in on the Smithsburg Road and General Jones’ was sent orders to come up to Hagerstown by way of Funsktown. While Richmond’s leading cavalry units were charging up Potomac Street, further north of Hagerstown, pushing Chambliss’ brigade toward Robertson’s brigade, Elder’s Battery went into position near the Female Seminary. Once Colonel Ferguson’s Brigade entered from the east, Elder’s Battery fired. Stuart had with him two guns from Jackson’s Kanawha Artillery.
The fighting was occurring in the streets, in church yards, cemeteries and Sergeant William Wilkin of the 1st West Virginia Cavalry recalled; “In one place, forty were sent to make a charge-not one ever returned.” Soon Jones’ Brigade came up with Chew’s Battery. Stuart’s cavalry already had artillery engaged; one of the guns of Mooreman’s Battery came close to being captured before it had the chance to be unlimbered, while a section of two guns from McGregor’s Battery were brought into action. These batteries eventually took position near the Reform Church and counter fired on Elder’s guns.
Upon arriving on the field, Stuart ordered Chew’s Battery to deploy. Private Charles McVicar recalled: “The enemy is here and opened. We replied with two guns.” While the fighting was occurring from the east and north, toward evening, General Alfred Iverson’s Brigade arrived on the field. Many of his North Carolinians took refuge behind stonewalls and filing into the streets. As the Union cavalry charge stalled, and without any additional reinforcements, Richmond’s command was being pushed back. Chew’s Battery moved several times and finally was able to get behind Richmond’s command.
As Buford was attacking Williamsport with Kilpatrick and a portion of Custer’s brigade, the Union attack on Hagerstown was doomed. In the streets of Hagerstown, the momentum had changed in favor of the Confederate cavalrymen and infantry that were engaged. Sergeant Wilkin recalled: “Till dark a running fire was kept up, the Rebels are pursuing us with great vigor.” Chew’s Battery doing damaged to Elder’s Gun made them change position a few times to the point their guns were in danger of being captured. There was a point during the Battle of Hagerstown that Chew’s two guns were thought to be finished. The soft ground beneath the cannon and due to the recoil and weight, the guns began to sink. The cannoneers saw a rail fence and tore the railing down. They soon started to pry the cannon from the ground and moved them and Chew’s guns were back in action.
The 11th Virginia Cavalry under the command of Colonel Lomax was situated in a field when the Battle of Hagerstown began. They saw two Union regiments drawn up along the road and protected by a stone wall and they had artillery posted upon the hill. As Colonel Lomax moved to the top of the ridge the enemy was hidden behind the stone wall. They soon charged and made contact but were forced to pull back. After Chew’s Battery began pounding the landscape, the 11th Virginia charged again. This time they sent the enemy fleeing. The apron flag bearer Watkins was wounded during the action. He hid the flag inside his jacket until he saw Captain McDonald and handed it over to him.
As the Union cavalrymen were falling back, Lieutenant St. Clair of the 1st West Virginia Cavalry was order to command the rear and to protect the artillery. Sergeant Wilkin was among those ordered to render Elder’s guns service. Sergeant Wilkin recalled: “In minutes the cannoneers were so thinned out that there were not enough left to man the gun; seeing which, I dismounted, and rendered what assistance I could in manning the cannon. It was hard work. Once I though we were almost gone, but a few more grape and canister sent them howling back and the gun was saved.” Joseph Lesage of Company G was placed in command in the extreme rear of the cavalry as it began to fall back.
As the Union cavalry was falling back, they were fighting every inch of the way. The Confederate cavalry finally gave up the pursuit after darkness had fallen upon the battlefield south of Hagerstown. Kilpatrick’s command as well as Buford’s command fell back to Jone’s Crossroads where it would rest and the following day they would fall back to Boonsboro. By July 8th, the two Union cavalry divisions would engage Stuart’s Confederate cavalry during the Battle of Boonsboro.