After the 1862 Maryland Campaign in September, many communities became one vast hospital and were in the process of recouping their losses. The Union army, still sitting idle from the bloody Battle of Antietam, was deployed throughout the areas of Pleasant Valley and Cumberland Valley. In early October, General Robert E. Lee ordered General JEB Stuart and portions of his cavalry to gather information about General George McClellan's army and harass his supply lines. This raid would be the first major Confederate movement north of the Mason Dixon Line.

On October 9th, 1862, General JEB Stuart and roughly 1,800 cavalrymen, along with four pieces of artillery began moving toward the Potomac River. The next morning, the Confederate cavalry force forded the Potomac River into Maryland at McCoy’s Ford between Williamsport and Hancock. By noon, the Confederate cavalry had entered Mercersburg, Pennsylvania. From there, Stuart turned toward Chambersburg, where he arrived after dark.

Upon enter Chambersburg, Stuart sent in a flag of truce to receive the town’s surrender. General Wade Hampton was given the opportunity to enter the city and no resistance was made. Most of the prominent citizens had already fled the city. The next morning, October 11th, Stuart managed to get some much needed supplies for his troops such as small arms, ammunition, and clothing. Stuart wanted to leave Chambersburg, and head toward Leesburg. Being assured that Cox’s Kanawha Division who was approaching Cumberland, Maryland would turn around and head toward Chambersburg, he thought it best to move toward South Mountain. General JEB Stuart left Chambersburg and rode toward Cashtown, where he learned that a Federal cavalry force was closing in.

To Stuart’s east and south, Colonel Richard Rush and his 6th Pennsylvania Cavalry were patrolling. Further to the south near Frederick, portions of Cole’s Cavalry were ordered to be on stand by. Several members of Cole’s Cavalry were from Frederick County. Union General Alfred Pleasonton and portions of his cavalry division, acting on intelligence, began pursuing Stuart’s cavalry from Knoxville, Maryland.

Since Stuart was in Pennsylvania, messages about a Rebel cavalry force had been sent over the wires. The communities that stood in the wake of the Battle of Antietam were now in a state of concern. An observation post was ordered to be established upon South Mountain at Washington Monument to see if Stuart would back track through the Cumberland Valley.

Upon reaching Cashtown, Stuart took the direct road leading to Fairfield where he took several stores of supplies, including several prisoners. From Fairfield, Stuart’s cavalrymen began heading toward the Mason Dixon Line. As Stuart was closing in on Maryland, 140 troopers of Rush’s cavalry had already been to Emmitsburg and were headed toward Gettysburg. Just as the advance of Stuart’s cavalry entered Emmitsburg, they charged the through the town chasing after the stragglers of Rush’s command. At just about sunset, Stuart and his cavalrymen entered and occupied Emmitsburg, Maryland.

The town of Emmitsburg hailed the Confederate troopers as the townsmen opened their arms to the Confederate cavalry. Many people of Emmitsburg applauded very loudly as the Confederate cavalry entered the town. Orders came from General Stuart to rest, feed and water the horses. As Stuart’s men began to mingle with Emmitsburg residents, they received fresh bread, buttermilk, and meat, and the town itself was being very supportive to those dressed in gray. Emmitsburg, at the time, had never really seen a Confederate soldier and the town was curious to hear the tales they had to tell. The men in the Confederate cavalry were noted as being polite to the residents of Emmitsburg. Major Henry B. McClellan observed General Stuart enjoying the hospitality of the local citizens of Emmitsburg, while he attended to his horse and stood up against a tree for about a half an hour before moving out.

Confederate Lieutenant Colonel W.W. Blackford, who was a captain during the 1862 Chambersburg Raid, noted they reached Emmitsburg at about sundown. General Stuart ordered pickets to guard the road leading out of Emmitsburg and capture anyone who attempted to leave. Blackford later wrote: "Just as the advanced guard entered the street, a young lady rode out of a yard of a house before us, and seeing, to her dismay, a body of soldiers, which she took for Federals of course, she dashed off out of town towards her home some miles in the country."

"Our men called upon her to halt, but this only made her whip up her horse the more, and being reluctant to use their firearms, the only thing to do was for two of the best mounted to overtake and capture her. It was an exciting race for a mile and the poor young lady was, as she told us, scared almost to death, but finding she could not escape she pulled up and surrendered in great terror. But when she and her captors appeared leisurely riding back they were in high good humor, laughing and talking over the adventure."

"The young lady returned to the house she had been visiting and was requested to remain there until we had been gone an hour. Though only a mile or two from the Pennsylvania state line, the people here seemed to be intensely southern in their sympathies and omitted no opportunity of showing us attention during the short half hour we passed among them."

Friendly citizens also greeted members of General Stuart’s Horse Artillery, as they paused long enough to feed and water their horses. Private Henry Matthews remembered the women of Emmitsburg: "Basket after basket of provisions was passed around." He continued: "The old battle scarred boys of the battery, with their farmers’ hats were indeed an object of curiosity to those sweet and dear ladies. Several boys could not resist the tender smiles of the fairer sex; I was one of the first victims, so we gave them our straw hats as souvenirs. I doubt not that some of those hats are still treasured by some of the ladies in that locality yet."

At this time, General Stuart ordered pickets to set up along the roads leading into Emmitsburg. A Federal courier was captured as the Union cavalry was closing in on the rear of the Confederate cavalry. General Stuart learned that Colonel Rush, and also General Alfred Pleasonton with some 800 members of his cavalry were pursuing him and were riding from Hagerstown toward Mechanicstown. The courier was then blind folded and released to fool Colonel Rush. General JEB Stuart attended to his horse and stood up against a tree for about a half an hour before moving out. Then the order was given to mount up. Fearing that General George B. McClellan knew his location, General Stuart left Emmitsburg shortly after sundown and headed for Virginia. Only a few stragglers stayed behind in Emmitsburg. Some reports state that Colonel Rush caught a few of these stragglers.

On the road toward Frederick, General Stuart accompanied Southhall, who commanded the advance guard. Before leaving him, General Stuart ordered him to keep up the fast gait and ride over any opposing parties. Soon after, another courier was captured carrying dispatches from Frederick to Colonel Rush’s Lancers. From this information General Stuart learned that even though the enemy was trying to intercept him, they still had no idea of his location or movements. He also learned that Colonel Rush had enough men in Frederick to protect the city, even though four companies of his Lancers were headed for Gettysburg.

The dispatches also stated that 800 men under the command of General Pleasonton was hurrying to Mechanicstown, just four miles from Stuart’s position and that the railroad crossing of the Monocacy was occupied by two brigades of infantry, ready at a moments notice to steam the railcar engines and deploy them in either direction.

With this new found information, General Stuart ordered the column to turn east at Rocky Ridge, Maryland and travel toward the Woodsboro Road, two miles away. At around 9:00 p.m., the advance guard reached Rocky Ridge where they met a scouting party of General Pleasonton’s Federal Cavalry, which turned immediately toward Mechanicstown. At a half past 10:00 p.m. a company of the 6th Pennsylvania Cavalry observed the march of General Stuart’s column through Woodsboro. This information of General Stuart’s location was dispatched to Colonel Rush, and then to General Pleasonton, who was only few miles away at Mechanicstown. Even though this information only had to go from Rocky Ridge to Mechanicstown, a mere four miles away, it took more than three hours to relay. In the meantime General Stuart continued his march toward the Potomac River.

By daylight of October 12, General Stuart’s advance guard entered Hyattstown, over 33 miles from Emmitsburg. General Stuart along with his men and artillery had traveled an amazing 65 miles within 20 hours. By this time members of Cole's cavalry caught up with the rear of Confederate cavalry. A skirmish developed and seven Confederate troopers were captured.