John Miller
Emmitsburg Area Historical Society

After Longstreet’s assault had failed on July 3rd, General Robert E. Lee, commanding the Confederate Army of Northern Virginia was forced to retire from the battlefield at Gettysburg. At around 11 o'clock that night, General Lee issued the orders for a withdraw from the battlefield. The majority of the Confederate Army marched through a mountain pass located on South Mountain called Monterey, about seven miles west of here. General John Imboden was charged with the wagon train of wounded and crossed South Mountain at Cashtown Gap. General JEB Stuart was given the task of screening the area toward Emmitsburg and Mechanicstown and then reporting to Leitersburg.

Union Cavalry Occupies Emmitsburg

While the Confederate Army was in the initial phases of their withdraw, Union Colonel Pennock Huey received orders to move to Emmitsburg for the purpose of taking possession and holding the town on July 4th. Colonel Huey is commanding the Second Brigade Cavalry of General Gregg’s Division along with the 2nd U.S. Battery M of the Horse Artillery.

Union General Judson Kilpatrick’s Cavalry Division consisting of General George Custer’s and Colonel Nathaniel Richmond’s Brigades arrived here with orders to destroy a Confederate wagon train moving through Monterey Pass. Meeting up with Colonel Pennock Huey, Kilpatrick orders his cavalry westward toward South Mountain.

Midnight Battle Erupts Upon South Mountain

On the evening of July 4th, 1863, during the retreat from Gettysburg, one of the most confusing battles of the Civil War occurs at Monterey Pass. Captain George Emack had a small detail of the Confederate 1st Maryland Cavalry guarding the approach to Monterey Pass. He was re-enforced by one cannon from Captain William Tanner's Battery. At around 9:00 pm Union cavalry under the command of General Judson Kilpatrick came in contact with this portion of the Confederate Maryland Cavalry under Captain Emack and it was here that the battle began.

Darkness set in during a blinding rainstorm. The Confederate artillerists, wearing gum blankets to protect them from the elements of the weather, had managed to disguise their identity from Kilpatrick’s men. Realizing that their identity was withheld, they open fired on the head of Kilpatrick's advance. As the confusion subsides, the Confederate cavalrymen charge, pushing Kilpatrick back until they reach the Federal artillery that is positioned near Fountain Dale.

For several hours, during the blinding thunderstorm in the middle of the night, the battle is carried out in between lightning strikes and muzzle flashes. After six hours of heavy fighting that had spilled over to Fairfield Gap and Leitersburg, General Kilpatrick gained the South Mountain summit of Monterey Pass. At Fairfield Gap, a portion of the 1st Michigan Cavalry is beaten back by Confederate cavalry while at the Monterey House; two guns of Pennington's battery began shelling the Confederate wagons.

By 3:30 am on July 5th, Kilpatrick successfully reaches the turnpike where Ewell’s wagon train was located, capturing and destroying 9 miles worth of wagons, taking 1,360 prisoners and a large number of horses and mules as they moved on toward Ringgold, Maryland.

Our Town Briefly Occupied by Rebel Cavalry

On the morning of July 5th, 1863, General JEB Stuart makes his way from the horrors of the fields of Gettysburg to our beloved town. General Stuart marches a brigade and a half of cavalry to Emmitsburg during the dawn hours with the 34th Virginia Cavalry under Lt. Colonel Vincent Witcher leading the advance into town. Near the old Hoffman’s Inn there is a sharp skirmish fought. Seventy Union men were taken prisoner in addition to numerous supplies such as medical items that would be used for the wounded Confederate soldiers who fought at Gettysburg.

It is reported to me that among the prisoners that were captured by the Confederates was a photographer from Mathew Brady’s Photography Firm. Three photographers, Alexander Gardner, Timothy O'Sullivan, and James Gibson all were traveling to Gettysburg when they came here to Emmitsburg on the night of July 4th. Gardner, himself stayed at the Hoffman Inn. At the time of my dispatch, it is still unclear which one of the three photographers that Stuart has captured, however, evidence suggests that it could have been Gardner. Mr. Gardner's fifteen year old son Lawrence is attending a boarding school just outside of Emmitsburg and it is believed that his father may have been assuring his son’s safety while he was held in captivity.

Stuart’s horsemen walked the streets, visiting the stores that were untouched by the fire on June 15th. These soldiers had no way of paying for the personal supplies that they received from our shopkeepers because Confederate money does not hold the value of green backs, and it is simply no good here in our northern region. Our poor store owners will be unable to recoup the money for what the Confederates took.

While the Confederates were watering their horses some of our residents struck up a conversation with them. Curious of the outcome of the battle of Gettysburg they asked Jenkins’ men who won the battle of Gettysburg. The soldiers quickly replied that they had won, of course. It did not take long before these same soldiers who claimed victory on the fields of Gettysburg became suspicious of some of our town’s people. On one occasion these trigger happy Rebels detected two gentlemen watching their every move, and suddenly the Rebels raised their pistols. They thought that these men were Union spies or were part of the Signal Corp. The two gentlemen quickly explained that they were villagers of our dear town and were curious as to what all the bedlam was about. Thankfully, the Rebels placed their guns back into their holsters, realizing that it was a false alarm.

Soon orders were given and Stuart’s Cavalry rode out of Emmitsburg during the mid morning hours. After leaving, Stuart’s Cavalry traveled toward Creagerstown on the direct road to Frederick or what is known as Old Frederick Road. At around noon, an hour and a half after departing Emmitsburg, Stuart came to an intersection. The roads of this intersection led to Rocky Ridge, Creagerstown and Graceham. Stuart sent a detachment to follow the rode to Graceham, while Stuart and the main body went to Creagerstown passing through Loy’s Station. Later that day, Stuart’s cavalry travels to Smithsburg where it clashes with Kilpatrick’s cavalry that was resting after the hard midnight fight at Monterey Pass.

Rejoice for those in Blue

On July 6th, portions of the main Union Army marched through our beloved town. Battle hardened men who fought gallantly for three days at the small town of Gettysburg, Pennsylvania. The men in blue were a site to see. Their uniforms wet from a rain that had begun to wash off the dirt and the smell of battle. One officer took a rest by a small stream and washed his feet and sunk his rank in the flowing water as if he was an enlisted man. Their spirits were high as they marched through town. The next day gave way to General George Meade, commander of the Army of the Potomac. Our citizens hailed him and thanked him for his dedication and service at Gettysburg.

Read Part 12: The Road to Smithsburg