On July 3, 1863, the Confederate army under the command of General Robert E. Lee suffered a major defeat at the conclusion of Pickett’s Charge. As the shattered remains of Major General George Pickett’s division made their way back to the Seminary Ridge, General Lee knew he had to prepare for the withdrawal of his army, as well as planning in case of a Union counterattack.

General Lee had much to plan for. He had vast amounts of wounded that were being cared for spread out from the west to the north of Gettysburg. He would have to plan for transportation of those men back to Virginia, providing they could make the journey. He had miles upon miles of wagon trains that contained the quartermaster stores, the ordnance, and commissary supplies for his army. Those wagons were scattered from Marsh Creek, south of the Fairfield Road to the northeast on Hunterstown Road, Hanover Road and York Pike. He had a reserve train parked several miles west of Gettysburg, which contained much of the bounty collected from Pennsylvania located between Fairfield and Cashtown. Lee studied which routes were available for his army to use in order to get to the Potomac River and to the safety of Virginia. Finally, he had to give orders to his infantry, artillery, and cavalry commanders.

General Lee looked over the maps to the options for roads to be used for his army. He could use Cashtown Gap, as he did when he crossed South Mountain, but another much shorter and direct route was the road to Monterey Pass. From there, the road led directly to Williamsport. Cashtown Gap and Monterey Pass, for the most part, were about 700 feet above sea level. The roads were macadamized, except for the Fairfield Road in the mountains.

The Cashtown Gap route would connect to several other roads. The Walnut Bottom Road connected to Pine Stump Road, which ran to Marion, Pennsylvania and connected to the Valley Turnpike. From the Valley Turnpike, the road led to Greencastle, Pennsylvania and a short distance to Williamsport, Maryland. But this route would add twenty miles in distance to Williamsport compared to Monterey Pass. Monterey Pass would be the route used for the majority of the Confederate army.

The only problem General Lee saw with Monterey Pass was the Emmitsburg and Waynesboro Pike, and the network of roads it connected to. The turnpike itself ran east to west, intersecting three major roads. The first road led directly to Fairfield, and ran through modern day Carroll Valley. The second road was Jacks Mountain Road. The third was the Fairfield/Hagerstown Road. locally known as the Maria Furnace Road. Maria Furnace Road connected to the Emmitsburg and Waynesboro Turnpike at the Monterey Tollgate. There, a series of roads also connected to the South Mountain pass. Situated between Jacks Mountain Road and Maria Furnace Road was Jacks Mountain itself. General Lee would instruct Brigadier General William Jones and Brigadier General Beverly Robertson to guard the roads to Monterey Pass.

Meeting with his top commanders, General Lee ordered Lieutenant General James Longstreet to remove Major General Lafayette McLaws’ Division and Brigadier General Evander Law, commanding Major General John Bell Hood’s Division from near the Round Tops back to Seminary Ridge. There, Lt. Gen. Longstreet was to build breastworks in case of a Union counterattack, attaching his right flank near the left flank of Hill’s Corps. Lieutenant General Longstreet was to guard the Confederate right flank from the south in case of a Union attack.

By 5:00 p.m., seeing the Confederate movements, Major General George Meade ordered the V Corps under the command of Major General George Sykes to move forward to conduct reconnaissance. The Union soldiers came under fire from Confederate artillery forcing the V Corps back.

Lieutenant General Richard Ewell was ordered to move his corps from Culp’s Hill, through Gettysburg, and redeploy his corps with his right flank on the Fairfield Road, and covering Seminary Ridge to Oak Hill. Ewell’s Corps would be the left flank of Lee’s army. He was to order Major John Harmon, who commands the Reserve Train, to move his train forward through Monterey Pass and get that train to the Potomac River. He was to also take personal command of Lt. Gen Ewell’s own quartermaster, commissary and ordnance trains.

General Lee ordered Lieutenant General A. P. Hill, who was already in position just west of Seminary Ridge, to extend his corps to the left of Longstreet’s Corps, holding the ridge line. His right flank would be positioned on the Fairfield Road. This would allow his corps to move onto the Fairfield Road first, followed by Longstreet’s Corps. Following the rear of the Confederate army would be Ewell’s Corps.

Major General J.E.B. Stuart was ordered to send out two brigades of cavalry toward Cashtown to screen the right flank of the Confederate army. He would also be ordered to screen the left flank of the Confederate army and move east of the Catoctin Mountain. The courier never arrived at Maj. Gen. Stuart’s headquarters and once Lt. Gen. Ewell began moving his corps, this left Stuart holding the left flank of the army with no infantry support. Major General Stuart rode to General Lee’s headquarters where Lee verbally gave Stuart his orders.

At 10:30 p.m., a courier was sent to Brigadier General John Imboden, near Cashtown. He arrived at Gettysburg near midnight. Being escorted to the officer’s meeting, Brig. Gen. Imboden was told to head to Lee’s headquarters and wait for him there. General Lee came in and the two officers met. General Lee ordered Brig. Gen. Imboden to organize the sick and wounded wagon trains and prepare them for their journey back to Virginia. He was also ordered him to oversee the wagon trains of Lt. Gen. Longstreet’s Corps and Lt. Gen. Hill's Corps, along with Maj. Gen. Stuart’s cavalry trains through Cashtown Gap. Their proper quartermaster officers would be in charge of their organization. A portion of Major General Richard Anderson’s divisional trains of Hill’s Corps would be redirected to follow behind Ewell’s trains through Monterey Pass.

General Lee also began solving the problems of transporting his sick and wounded. There was a shortage of ambulances and wagons. He ordered a courier to Winchester, Virginia with news of the shortages. General Lee then ordered his quartermaster, commissary, and ordnance officers to spare any wagons that could be used for transportation. Off loading and compiling any supplies to free up any wagons.

The situation in regard to the hospitals at Gettysburg was a complicated one. As the battle unfolded at Gettysburg, and hospitals were established, the ambulances were under the control of the quartermaster. Additional detachments of wagons themselves were scouring the countryside for supplies. By July 3, wagons upon wagons were parked all over western and northern Gettysburg. General Lee needed time for those wagons to assemble for the journey back to Virginia.

Lieutenant General Longstreet’s Corps quartermaster stores were situated west of Gettysburg. Major General McLaws’ divisional wagons were parked in the fields near Marsh Creek. Major General George Pickett’s divisional wagons were located near Marsh Creek, south of the Fairfield Road. The divisional wagons of Major General John B. Hood were located on the Fairfield Road at Willoughby Run.

Lieutenant General Ewell’s Corps was spread out as well. The quartermaster wagons were located to the northwest and north of Gettysburg. The divisional wagons for Major General Jubal Early were located in the fields between the Harrisburg and Carlisle Roads. Major General Allegheny Johnson’s trains were located in the area of Hunterstown Road, York Pike, and Hanover Road. Major General Robert Rodes’ wagons were near the Mummasburg Road.

Lieutenant General Hill’s Corps wagons were located northwest and west of Gettysburg, more or less along the Chambersburg Pike. Major General Richard Anderson’s divisional wagons were located along Herrs Ridge Road. Major General Henry Heth’s wagons for his division were located the Chambersburg Pike near Seven Stars. Major General Dorsey Pender’s divisional trains were located at Seven Stars. The Reserve train under the command of Major John Harmon was located near the base of South Mountain between Cashtown and Fairfield. Major General Stuart’s trains were located along Hunterstown Road.

Assisting the quartermasters were contracted civilians, some enlisted men and African-Americans. It is estimated that at least 6,000 to 10,000 African-Americans were attached to the wagon trains. They were the teamsters who controlled the teams of horses and mules used to pull the wagons. Many were servants who were forced into the military by their masters. Several were armed for the protection of the trains.

At Falling Waters, forty-five miles to General Lee’s rear, was the pontoon train. It consisted of sixteen flat bottomed wooden pontoons, about thirty feet wide. Included with the pontoon train were the trestle work transport vehicles. Guarding this temporary bridge was a detachment of infantry, teamsters, and engineers. Prior to the invasion of Pennsylvania, none of the Confederate army used this crossing. Early in the morning of July 4, Federal cavalry burned and destroyed this temporary bridge and captured the guard detachment.