While the Confederate army was marching out of Frederick toward Hagerstown, many cavalry detachments picketed the Catoctin and South Mountains. On September 12th, as Confederate General JEB Stuart bivouacked near Middletown, he had left the Jeff Davis Legion to guard Braddock Gap in order to protect his wagon train, and to keep an eye on Union soldiers that may appear from the direction of Frederick. To the south portions of Colonel Thomas Munford’s cavalry was guarding the approach to Jefferson, near Jefferson Pass.
To the north of Braddock’s Gap lay three other mountain passes. Shookstown Pass, which was located on the Baltimore Road, High Knob, a rough and rugged mountain pass, and then there was Hamburg Pass. Hamburg Pass overlooked the valley between Lewistown and Frederick. The Frederick Road that ran through this area was a major artery that took inhabitants from Frederick to Emmitsburg and across the Mason and Dixon Line into Pennsylvania.
On the morning of September 5th, the gray-clad soldiers forded the Potomac River into Maryland at Edward’s Ferry. Edward’s Ferry is downstream from White’s Ford. The cavalrymen were ragged, some were even barefoot in the saddle. In Maryland they managed to buy boots, shoes and clothing, paying the merchants in Confederate money. While encamped at Barnesville they were ordered to attack a detachment of Union soldiers, who from their location at Sugarloaf Mountain, could see all of the Confederate movements. From there they were ordered to Frederick.
On the night of September 12th, the 4th and 9th Virginia Cavalry left Frederick, as they were ordered to the Catoctin Mountain. East of Hamburg, the 3rd Virginia Cavalry, 4th Virginia Cavalry and the 9th Virginia Cavalry picketed the mountain gap to watch for troop movements leaving Frederick. The town that the gap is named after no longer stands, but during the Civil War it was a small mountain community. Today ruins can bee seen in the woods in the park boundaries of Gambrill State Park.
During the evening of September 12th, Union General Alfred Pleasanton made his headquarters at Frederick. General Ambrose Burnside had arrived a half hour prior, after marching on the New Market Road. The brigade of cavalry under the command of Colonel John Farnsworth had bivouacked west of Frederick, while portions of the 6th Pennsylvania Cavalry, and a section of artillery ordered to Jefferson to meet up with General William Franklin’s Sixth Corps who were bivouacking to the east of the Catoctin Mountain.
Early the next morning, General Alfred Pleasanton ordered a section of Lieutenant R. Hunter Chapin’s 3-inch Rifles of the 2nd U. S. Artillery, Battery M, and the cavalry brigade of Colonel Andrew T. McReynolds to scout the Emmitsburg and Gettysburg areas to see if the Confederate army was moving into Pennsylvania. Under his command were two regiments of cavalry, Major James A. Congdon’s 12th Pennsylvania Cavalry, and Major Alonzo W. Adams’ 1st New York Cavalry, nicknamed the Lincoln Cavalry.
Pleasanton was to find the rear of the Confederate army. As the sounds of artillery broke the silence of the day six miles to the south at Braddock’s Gap, the troopers near Hamburg Pass were enjoying their duty. They soon received an order from General JEB Stuart to move east of the Catoctin, and try to turn the Federal right flank. They mounted their horses and moved rapidly toward Frederick to the New Market Road.
As the 4th Virginia Cavalry, supported by the 9th Virginia Cavalry, moved they came into view of the 1st New York Cavalry as it moved to Emmitsburg. The Virginians attacked the rear of the Federal column. Within minutes, nine Union troops and one ambulance fell into Confederate hands, although another account states that two ambulances were taken. As the fighting quickly began to die down, several Confederate troopers were taken prisoner. After the fight, the 1st New York proceeded to Emmitsburg where they encamped for the night.
Realizing that the majority of the Union army was encamped in and around Frederick and moving toward Braddock Gap, the troopers fell back to the eastern base of the Catoctin Mountain. There the Confederates remained in a line of battle until midnight. They were ordered to proceed back up the mountain and arrived at Hamburg just after 10:00 am on September 14th. As the Confederate soldiers passed through Hamburg, Sergeant George Beale of the 9th Virginia Cavalry noted the condition of the town, simply stating “Hamburg was a rude and scattering village on the crest of the mountain.”
Sergeant Beale also noted “The manufacture of brandy seemed to be the chief employment of the villagers, and at the early hour of our passage through the place, both the men and women gave proof that they were free imbibers of the product of their stills, and it was not easy to find a sober inhabitant of either sex.”
The Confederate troopers didn’t receive a very warm welcome at all. Lieutenant Colonel Richard L.T. Beale of the 9th Virginia Cavalry wrote “A party of women seemed amused and delighted at the ragged outfit of our men, and were certainly as intensely hostile as any blue-stocking “school marm” of Massachusetts.”
As the Confederate troopers passed through Hamburg, they began to descend Catoctin Mountain. There, the valley in the distance opened up, giving the soldiers a spectacular view of the fertile farmlands in what Sergeant Beale described as “A scene of unusual beauty and loveliness.”
As the Confederate soldiers came to a large grist mill, orders were given to halt. After a march of several hours on horseback, they rested in an apple orchard which provided them with shade. There they finally received rations and soon began to prepare them. This was the first time they had received them in two days. The troopers also took time to attend to their horses.
The men heard the sounds of battle taking place on the next ridge over at South Mountain. At 4:00 pm, the troops were ordered to mount up, and to head toward the town of Boonsboro, where they rested again after nightfall. Soon afterwards, they would be ordered on standby as the Confederate infantry retreated off of South Mountain, pouring into Boonsboro. Sergeant Beale noted “The nature of the ground was ill-suited to the operation of cavalry, and much relief was felt when, at dawn [15th], we began to fall back towards Boonesboro.”