A soldier and later historian of the Twelfth Massachusetts Volunteers recorded a story about a young boy from Emmitsburg, Maryland.  Later in life he wrote: 

“An instance of the bravery of an 15 year old Emmetsburg lad named J. W. (C.F.) Wheatley,  as Baxter’s brigade was marching through Emmetsburg it was followed by the village boys, one of whom continued to the camp at Marsh Creek, where he offered to enlist. His offer, however, was ridiculed, and he was sent away. On the morning of the 1st of July he reappeared, and so earnestly entreated the colonel of the Twelfth Massachusetts to be allowed to join his regiment, that a captain of one of the companies (Company A) was instructed to take him on trial for a day or two. When the regiment halted near the seminary, the boy was hastily dressed in a suit of blue.

Afterwards, during the action, he fought bravely until a bullet striking his musket split it in two pieces, one of which lodged in his left hand and the other in his left thigh. The boy was taken to the brick church in the town to be cared for, but nothing was afterwards seen or heard of him until July 4th.  I saw him for the last time bitterly crying for his mother and sundry of other relatives.  He was never muster into the service, therefore fought as a civilian."

Emmitsburg was being devitalized of its own surplus as both forces came into Emmitsburg in July of 1863. Emmitsburg had lost a great deal of supplies due to the fire that had occurred on June 15^th of 1863. When the armies came through town, they were confiscating what little Emmitsburg had left. The roads were being torn apart by wagons, horse drawn artillery, and soldiers who marched through the town during a rain storm. Roads around and in town were flooded with troops pursuing the rebels as they marched home to Virginia. 

Lieutenant Colonel A. Dobke, Commanding the Forty-fifth Regiment New York Volunteers recalls the road conditions and also the troops morel during the pursuit of the Confederate Army.  He wrote:

“After the battle (Gettysburg), the regiment remained on the battlefield on Cemetery Hill until 6 p. m. July 5, when it marched off toward Emmitsburg. At midnight the march was stopped, owing to the complete darkness and the horrible condition of the roads, which were nearly impassable from the heavy rain of the last two days. At 4 p. m. on July 6, the regiment arrived at Emmitsburg.

On July 7, the heaviest march of the campaign was executed, marching 32 miles from Emmitsburg, and arrived at 10 p. m. at Middletown, a distance of 34 miles, through the open fields, taking a narrow pass road over the mountains in a circuit. Toward night the rein descended in torrents, amid which men and beasts sank down, tired to death, most of the soldiers without any shoes, barefooted, or shoes so ragged or torn that they did not deserve the name.”

The Confederates that came into Emmitsburg had no way of paying for the personal supplies that they received from the town due to the fact that Confederate money did not hold the value of green backs, and Confederate money was no good in this northern region. This meant that Emmitsburg couldn’t make a profit no matter how hard the town had tried. As the Army of Northern Virginia retreated some of its companies came through Emmitsburg and settled in for the night by Tom’s Creek near the present day U.S. Post Office.

On Sunday, July 4^th, Confederate cavalry under the command of General Albert Jenkins came into Emmitsburg. General Jenkins was patrolling around the wagon train that was in Fairfield at the time when he came into Emmitsburg. While watering their horses, residents who were curious of the out come of the battle of Gettysburg asked the troopers who won, their reply was that the Confederates had won. The Confederate riders also became paranoid by some of this hamlet’s residents. 

On one occasion some rebels detected two gentlemen watching every move they had made, when suddenly the rebels raised their pistols. These rebels thought that the gentlemen were Union spies or were part of the signal corp. Once the two gentlemen explained that they were villagers of the town and were curious as to what all the bedlam was about, the rebels placed their guns back into their holsters. 

Farms in the area were also being raided for their horses. On one occasion, Confederate soldiers halted by a local mill and were in the process of taking the mill horses when the miller became aware of what was happening and ran outside and yelled "You can’t take my horses, I need them for my work." The soldiers told the miller that they needed them badly to get back home, and if they could use them to get to Hagerstown and across the Potomac the miller could have them back. So the miller went with the troopers and brought the horses back to his mill several days later. Soon the rebel cavalry left Emmitsburg to rejoin General Jones up at Jack’s Mountain.

On that same day General Kilpatrick’s men came riding into Emmitsburg at a full charge, hoping to find the parts of the Confederate cavalry in town. They were soon disappointed, for there were no rebels to be found. When General Kilpatrick arrived in town the Union cavalry proceeded to rest for a bit and get something to eat. The town had given away all the tobacco and most of the bread. Most of the medical supplies that the town had were being used to treat men who were wounded. Once General Kilpatrick learned of the movement of the Confederate cavalry only five miles away at Monterey Pass, the Union cavalry left Emmitsburg late in the afternoon and began to pursue the Confederate wagon train.

On July 5^th, General Stuart came through the town of Emmitsburg during the dawn hours, where he heard that a large Union cavalry under the command of General Kilpatrick had just left the town only hours before his arrival. The Union cavalry was headed toward the rebel wagon train on Jack’s Mountain. General Stuart also learned that the route he wanted to take to get back to General Lee was in the same direction that the battle of Monterey Pass had occurred when General Kilpatrick left Emmitsburg. 

After coming into the western side of Emmitsburg, General Stuart engaged in a small skirmish near the Farmer’s Inn taking seventy Union soldiers as prisoners. General Stuart also captured large quantities of medical supplies that the rebels needed from the convents in Emmitsburg. Once General Stuart got their required supplies needed, they left traveling down Old Frederick Road toward Mechanicstown. 

Once in Mechanicstown, Stuart learned that General Merrit’s U.S. cavalry occupied Harman’s Pass. The Confederate cavalry left Franklinville, trying to pass the Catoctin Mountain range. According to a Union Signal Officer, General  Stuart came back into Emmitsburg, skirmishes developed when he tried to get over the present day College Mountain. 

"During the late movements of the army, 3 signal officers and 6 flagmen were captured by the enemy. The only reported injuries were those of 2 flagmen slightly wounded at the battle of Gettysburg. The capture of Captain B. F. Fisher, chief acting signal officer, has been previously mentioned. Captain C. S. Kendall and Lieutenant L. R. Fortescue, acting signal officers, were taken at Emmitsburg, where they had been on station, by Stuart's cavalry upon their retreat from Gettysburg, July 5."

General Stuart did however manage to check his counter parts and force them back into Emmitsburg. The Confederate cavalry had gotten away, thus beginning their journey home to Virginia.  General Stuart wrote in his report of the retreat from Gettysburg as follows: