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The Emmitsburg and Waynesboro Pike

By John A. Miller, Emmitsburg Historical Society

The Emmitsburg and Waynesboro Pike was a major road that traveled over South Mountain and had several key intersections that connected to it. Zora was only a crossroad at the time of the Civil War. It was where the Emmitsburg-Waynesboro Road and the Fairfield Road came together, and both armies felt the need to obtain and protect their positions at these crossroads and mountain gaps.

Midway between Emmitsburg, Maryland and Waynesboro, Pennsylvania was a mountain pass called Monterey. During the Civil War soldiers from both side felt it necessary to keep this road open for communication and observation. Scouts and pickets used the crossroads to see the troop movements that came from the direction of Emmitsburg, Waynesboro or Fairfield.

On June 15, 1863, Brigadier General Albert G. Jenkins, with 1,600 cavalry entered Pennsylvania and advanced on Greencastle where he divided his cavalry brigade. On June 19th, Company D of the 14th Virginia Cavalry was ordered to Waynesboro to capture horses and cattle for the army. The next day the men were foraging and around noon Company D came upon a farm of an old Pennsylvania German. According to Lieutenant Herman Schuricht; "He was scared to death at catching sight of us, and shouted "O mein Gott, die rebels!" I soon reassured him, telling him that no harm should result to him if he furnished us with a dinner and rations for our horses, and we were well cared for.

On June 22nd a skirmish erupted at Monterey. Company D of the 14th Virginia Cavalry ran into an armed militia of Captain Robert Bell's 21st Pennsylvania, Captain David Conaughy's Home Guard and a detachment of 1st Troop Philadelphia City Cavalry under Captain Samuel Randall. Confederate skirmishers scoured the woods on foot on each side of the Emmitsburg and Waynesboro Turnpike. When the Federal Cavalry left, the Confederates reached Monterey Springs and continued firing at several bodies on horseback and enter Fairfield at Dusk.

Six miles north of the Mason and Dixon Line is a little town called Fountaindale. Fountaindale is located between Jack's Mountain, Beards Hill, on the Old Waynesboro Pike. Pegram's Artillery reached Maryland late in the evening on June 25th, crossing the Potomac River at Boteler's Ford. From there they traveled the roads that led into Hagerstown. Private John C. Goolsby who was a member of Crenshaw's Artillery recorded "We pushed on and soon struck the village of Waynesboro, where United States flags were displayed in great numbers, which, of course, we greeted pleasantly. Another day's journey brought us to the foot of Cash Mountain, where we had several men captured. "

By the time that parts of Pegram's Artillery Battalion had encamped at Fayetteville they had lost several horses. Because of the concerned state the horses were in, Lieutenant John Hampden (Ham) Chamberlayne led a small detail soldiers from Purcell, Crenshaw, and Lecture's Batteries and made their way through Franklin County into Adams County where they came to Fairfield.

From Fairfield, Chamberlayne's men traveled toward Monterey when they came across a small church at Fountaindale on June 28th. A small Lutheran Church, located on Old Waynesboro Pike near present day Jacks Mountain Road is where the encounter of Fountaindale took place. It was Sunday and church services were underway. Ham Chamberlayne saw about 20 horses tied to a post and decided that these horses were are exactly what his battery needed.

As Chamberlayne's men started for their camp, a detachment of the Keystone Rangers was spotted coming down Waynesboro Pike. This was a small squad of horsemen under the command of Lt. William A. Horner. Seeing rebel horsemen near the church Lt. Horner, order his squad to halt near a brick school house near the Lutheran Church and try to intercept them.

It was at this time that Ham Chamberlayne hand-selected 6 men who had revolvers to turn and make a stand with him, while the others made their escape. Chamberlayne led his men directly toward Horner's men and charged. A clash erupted between these two forces. Private Goolsby mentions the small detail fell back to it's main party. After the charge, Chamberlayne and his six men were taken prisoner. After the skirmish, Horner's Keystone Rangers retired with their prisoners to Emmitsburg. During the evening of June 28th the Federal Cavalry under General John Buford came into Fountaindale moving toward Fairfield, investigating the rebel forces in the area.

By June 29, General John Buford stood at the opening of Monterey Pass which overlooked the Cumberland Valley and saw the Confederate Army in Greencastle. It was at this time that he suspected a battle would soon erupt in south-central Pennsylvania. That evening General Buford counter-marched back toward Fountaindale, and on the highest point he looked down the valley toward Fairfield, and saw the campfires of those troops belonging to General Henry Heth's Division.

On the evening of July 4th, one of the most confusing battles of the Civil War occurred during the retreat from Gettysburg known as the battle of Monterey Pass. General Robert E. Lee had given the order to retreat from Gettysburg. During this retreat General Ewell's Confederate wagon train took the road leading over Jack's Mountain from Fairfield.

Around 9:00 p.m. near Fountaindale, Pa. the Union cavalry under the command of General Kilpatrick came in contact with the Confederate 1st Maryland cavalry under Captain George Emack, who had a small detail guarding the approach to Monterey, re-enforced by one cannon that was loaded with two rounds of ammunition.

Darkness set in during a blinding rainstorm. The Confederates wearing gum blankets were mistaken as Union troops by Kilpatrick's cavalry as they made their way from Fountaindale. Knowing that their identity was withheld, the order came from Emack to fire the cannon. As the confusion subsided, the Confederates charged, pushing the Federals back until they reached the Federal artillery that was at Fountaindale.

General Kilpatrick gained the mountain summit of Monterey six hours capturing and destroying 9 miles worth of wagons, taking 1,360 Confederate prisoners and a large number of horses and mules as they moved on to Waterloo.

On July 5, General Meade issued orders for the Army of the Potomac to begin its removal from the battlefield at Gettysburg. By July 6, General Meade ordered General Howard to move one of his Corps to Emmitsburg and the other Corps to be posted on a road leading to Fairfield. According to General Meade, after receiving information on the Confederate Army's retreat route, all evidence showed that the principal force was between Fairfield and Hagerstown moving toward the Potomac River.

By 9:00 a.m., the Confederate Infantry, numbering about 80,000 men, was reported to have passed the Fairfield Road. General Meade learned that the Waynesboro Road was empty when parts of his army arrived. General Meade advised his Corps Commanders that he would continue his flanking movement once the main Confederate Army had retired from the mountain. With this plan, he directed General Couch's Cavalry to move down the Cumberland Valley and threaten the Confederate rear.

General Pleasanton ordered a brigade of Cavalry, under Colonel McIntosh to communicate the Confederate troop's movements as his Cavalry traveled toward Waynesboro. General George Sykes, commanding the Fifth Corps wrote to General Howard during the evening, explaining his position. He was located near the junction of the Emmitsburg Pike and the Fairfield Road. He had not heard word from General Sedgwick on troop movements and had not received orders from General Meade or from his wing commander, General Howard. A sign of frustration along with the lack of communication was taking its toll on the Union Army.

During the Raid on Washing in June and July of 1864, Union Cavalry patrolled the Emmitsburg and Waynesboro Pike. By late July, General Early ordered his army North, and splitting his army into two columns. The first column under the command of General John McCausland was sent forth to Chambersburg, PA, while the second column under General Early himself set forth to Moorefield W.V. Some independent Confederate Cavalry units operated independently along the Maryland Border. The Union Army took action in protecting it's communities along the Mason and Dixon Line.

On July 30, around 11:30 a. m. General H. W. Halleck sent word to General Hunter that as of 3 a.m. the enemy entered Chambersburg in three columns. A detachment of Hunters Cavalrymen was ordered to march by South Mountain toward Emmitsburg. General Halleck stated that it was absolutely necessary that he know where the Confederates were marching to in order to send re-enforcements. By 3 p.m. General Halleck sent another dispatch to General Hunter stating that Clendenin's cavalry was ordered to scout toward Emmitsburg and send back information on rebel force that entered Chambersburg. Meanwhile, General Lew Wallace sent a detachment of the Twenty-first Pennsylvania Cavalry, under the command of Captain J. C. Hullinger to march to Waynesboro via Emmitsburg. Also a Signal Camp was opened at Emmitsburg by Chief Signal Officer Amos M. Thayer relaying messages to the cavalry stationed at Emmitsburg as they waited.

In his report; Captain Franklin E. Town who was the Chief Signal Officer during the Operations of the Shenandoah Valley stated on July 31st, he had reached Frederick, Maryland and sent Lieutenant Ellis to Emmitsburg to communicate with Captain Thayer (Also a Signal Officer) and order him to go to Chambersburg and report the operations of the enemy there. A line of communications was made along the Mason and Dixon Line which kept General Crook in communication with headquarters during his march toward Emmitsburg. On August 1st, Lieutenant Ellis reported from High Rock that Chambersburg was burned; General Couch had returned to Carlisle, and General Averell was at Greencastle and was headed toward Gettysburg. On the 2nd of August, Lieutenant Ellis returned to Frederick from Emmitsburg.

By the afternoon, a skirmish erupted at Emmitsburg as a percussion from the Burning of Chambersburg. A small contingent of Union Cavalry guarding the area around Emmitsburg was driven into Emmitsburg by superior numbers of Confederate forces. A detachment of Philadelphia City Scouts operating in the area captured a considerable number of Rebels and among those arrested a few days ago was a brother of the celebrated General Stewart, of raid memory. He was taken near Emmitsburg by two or three of the scouts from Philadelphia, one of whom was a physician, and had been in the same medical class at Philadelphia with the Rebel spy arrested (Dr. Stewart.) He accosted the Stewart familiarly by name, when he came up to him. The latter denied all knowledge of his captor, but finally confessed that he was the man.


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