The Battle of Monterey Pass: The Quartermaster’s Nightmare

During the last two years, I have had some really good questions asked about the wagon train that traveled through Monterey Pass. Such questions have now prompted me to write a little piece about the Confederate wagon train that traveled through Monterey Pass. In my opinion, nowhere in Civil War history is there a retreat more important, or conducted as gallantly than that of the Confederate withdraw from Gettysburg. I have been intrigued by this story for more than ten years now.

Before we get to the quartermaster’s role during the retreat from Gettysburg, there are a few things that I want to discuss first. Many people often make the statement that many historians, due to time restraints when we give talks, fail to give a total picture of what the scene with these wagons may have looked like, how big they were, and was there more than one style of wagons that were used in the American Civil War, more so during the Confederate Retreat from Gettysburg. I want to quickly break down the role of the quartermaster and what that area of the army did. I also want to discuss the average wagon and ambulance that may have traveled through Monterey Pass as well as the driver, himself.

On February 26, 1861, the Confederate Quartermaster’s Department was organized by an act of the Confederate government as a key position. Among the other key positions was that of the Commissary General of Subsistence. The Quartermaster’s Department was responsible for clothing the regular army. The volunteers of the Confederate army were part of the commutation system, which meant that the volunteers and state governments were to provide their own uniforms and the Confederate government would reimburse those soldiers. Due to issuance problems, the commutation system ended in December of 1862 when the Confederate Government’s Quartermaster Department took over. This is also known as the Depot System. In some cases it was until mid 1863 when the commutation system was officially phased out.

So who was the Quartermaster and what were their duties? The quartermaster was responsible for the issuance of clothing, supplies, horses and means of transportation, whether it be on land or by water. Their wagons also carried the baggage of the men depending upon what the marching order called for. For example, during a forced or a light march, knapsacks and extra items would be hauled in the regimental wagon. In order to section out the many responsibilities of the quartermaster, his department was broken down into three categories: clothing, camp and garrison equipment, transportation, and supplies for the army.

The first category, clothing, camp and garrison equipment was in charge of the extra uniforms, personal items of the soldiers, and garrison equipment such as cooking items. During the wagon attack at Monterey Pass, you learn that many of the artillery kitchen items and camping gear were destroyed. Many of the extra uniforms and personal items of the soldiers were among the wreckage of those wagons burned by Union cavalry or contained in the wagons whose teamsters fell from the edge of the mountain road in the chaos of battle.

The second category was that of transportation. The transportation, whether it be on land or water, was important. In the case of the Confederate army when it invaded Pennsylvania, supplies were carried by means of a wagon train. The wagon train was under guard and hung back toward the end of the infantry. In the Union, one army could contain about three thousand wagons pulled by a four-mule to a six-mule team. Each regiment or gun of a battery was allowed one wagon. Each brigade was allowed ten wagons. Among this category, hay and feed for the animals were also carried. Headquarters for the brigade, divisional, corps, and the main army would most likely fall under this category as well.

The last category of the quartermaster department was the supplies for the army and the department. This area of the quartermaster issued out hospital supplies, fuel, equipment and other odds and ends. It was also responsible for the issuance of barracks and quarters, as well as providing necessary supplies such as building materials, glass, rope, and nails. Personnel would be clerks, laborers and cooks.

According to the article “Mule-Drawn Wagon Trains” by Dick Crews, the average size of a wagon body was about ten feet long, with a canvas top attached to the wagon. The wagon also had a toolbox located in the front and a feedbox, with a grease bucket and water bucket to the rear. In wagon parks repairs and maintenance were often conducted with skilled laborers of all trades making the repairs.

When it came to the grunt work of pulling the wagons, mules were often the best choice. Mules are a lot stronger than horses and could pull the wagons over muddy and rough surfaces. Mules could also take the hard treatment from the demand placed upon them moreso than horses. Once the mules were harnessed to the wagon they were paired into three teams. Toward the front were the lead pair; the pair in the center were known as the swing pair; the pair closest to the wagon was the pole pair. The driver himself was positioned on a saddle placed upon the left rear mule and were typically unarmed, as was the case during the Battle of Monterey Pass.

In addition to the wagon train itself, you had several other wagons that followed. Ambulances, artillery forage and battery wagons, and supply wagons. Ambulances, depending on their body style, could average from ten to thirteen feet long. Of the supply wagons you had the Commissary General of Subsistence who was responsible for the issuance of rations to the soldiers. The Ordinance Department also had wagons with supplies of ammunition. And following all of these wagons were extra horses and mules.

During the Maryland Campaign of 1862, many of the Confederate wagons were parked near Beaver Creek, and some down near Pleasant Valley. During the night of September 14, many mounted troops that escaped the surrender of Harper’s Ferry came upon Longstreet’s supply wagons and captured about sixty of them and took them to Chambersburg. During the Pennsylvania invasion of 1863, you hear about foraging wagons, ambulances, and supply wagons of all sorts being used, and in the case of the Battle of Monterey Pass, being captured or destroyed. Even during Confederate General Jubal Early’s Raid on Washington, there are supply wagons as well. But you usually don’t hear about those wagons unless they were captured by General JEB Stuart or they were attacked at Monterey Pass.

After reviewing the three main areas of the quartermaster, the ordinance and commissary supplies, I will try to reconstruct the wagon train of General Richard Ewell’s Corps as it traveled through Monterey Pass during the afternoon and evening of July 4th into the morning hours of July 5th, 1863. From what history shows, General John Imboden was tasked with leading the wagon train of wounded and the wagons of Hill’s and Longstreet’s Corps through Cashtown Gap.

General William Jones was ordered to lead Ewell’s wagon train out of Pennsylvania as well as to protect the roads. Ewell’s wagon train was roughly seventeen to twenty miles long and contained much needed supplies that were gathered during their travel toward Carlisle, before the first shots of Gettysburg were fired. Among the wagon train was about 3,000 head of livestock, produce from Pennsylvania farms, and a sizeable amount of freed blacks that were to be sent back to Virginia as contraband. Ewell’s wagon train traveled from Black Horse Tavern with Johnson’s divisional wagons in the lead, followed by Early’s divisional wagons, and ending with Rodes’ divisional wagons. The wagons were to travel to Williamsport, where they would cross the Potomac River and seek safety on Virginia soil, a distance of more than forty-five miles.

Escorting the wagon train was the 6th Virginia Cavalry, four companies of the 1st Maryland Cavalry, two companies of the 11th Virginia Cavalry, and the 4th and 5th North Carolina regiments of cavalry. Among the artillery was the First Rockbridge Artillery, a section of Mooreman’s Battery, and Chew’s Battery. The First Rockbridge positioned itself at the crossroads and the heights of Monterey Pass, but was eventually withdrawn and ordered to position itself at Burn’s Hill located in Waynesboro. The 1st North Carolina Battalion of Sharpshooters and two companies of an Alabama unit escorted and served as provost to the wagons, and several Confederate deserters. Captain William Tanner, by a stroke of luck, came up the Emmitsburg and Waynesboro Turnpike and saw no artillery support east of Monterey Pass. Tanner ordered one cannon to deploy, sending the other four pieces of his battery to Waynesboro.

The wagon train had to cross over the rugged South Mountain range through two main gaps. The first was Fairfield Gap and from there, about a mile and a half away, was Monterey Pass. Looking at South Mountain, there is no other mountain gap or pass situated like that of Monterey Pass. Monterey Pass was a very important transportation route. Five major roads intersected there, making it an essential crossroads. A toll house connected these roads which were at the time: the Emmitsburg and Waynesboro Turn Pike, with the Waynesboro side of the turnpike macadamized; the Fairfield Road or Maria Furnace Road, as it is known today, leading from Monterey Pass to Fairfield Gap; Mentzer Gap Road that took you to Quincy, located near Waynesboro, and eventually leading to Chambersburg; Pennersville Road that took you to Maryland, about one mile away. Near the intersection of Pennersville Road and the Emmitsburg and Waynesboro Turnpike, was another fork that followed parallel to the Emmitsburg and Waynesboro Turnpike leading to Buena Vista Gap.

If Monterey Pass would come under attack by Union troopers, and it was held by such a force, it could force the Confederate army to redirect its line of march, taking longer to get out of Pennsylvania. It could possibly force Lee to take another route in unfamiliar territory, something that Lee could not afford to do. Everything for the Confederate army and its withdraw depended upon their success or failure at Monterey Pass.

To make matters worse, during the afternoon of July 4th, it began to rain in torrents. Heavy downpours and heavy wagons turned dirt roads into a muddy nightmare. The rain and road conditions were bad enough for the troops but to add to that the road that they took from Fairfield, winding up South Mountain, leading up to Fairfield Gap was a rugged narrow road. Even though the map shows that this was the shortest and most direct route to Williamsport, this road would be considered by many Confederate soldiers as “Mount Misery” or “Quagmire.”

One problem presented itself immediately upon entering Fairfield Gap, and that was the fact that horses and mules had an exhausting trek up the mountain. Many horses simply dropped to the ground unable to carry the load, or even worse, the horse or mule dropped dead in the middle of the narrow road creating what is known as a traffic jam in modern terms. The narrow road would force teamsters to remove the carcass and move on the best they could and as quickly as they could. In some instances, axles would be cracked as was the case with many of the artillery carriages. As long as the wagons were moving, the quicker they would clear South Mountain.

As night fell, the teamsters riding on the wagons found it increasingly difficult to navigate in the darkness along the rugged mountain leading from Monterey Pass to Waynesboro. As lightning flashed, it would temporarily blind the horses, causing even more chaos. At the base of South Mountain is a little community called Waterloo. Many wagons were parked there while other wagons traveled through Waterloo to Rinngold, Maryland. The wagons then entered Leitersburg and headed to Hagerstown.

During the day as the wagons were moving along, General Judson Kilpatrick was ordered to harass and get ahead of the wagon train, reaping as much destruction to those wagons as possible. As the Battle of Monterey Pass began around nine o’clock in the evening of July 4th, Union cavalry of General Kilpatrick’s Third Cavalry Division attacked the Confederate forces east of Monterey Pass. More than six hours of fighting raged in the middle of the night during a severe thunderstorm. After the first initial contact, Captain George Emack, commanding Company B of the 1st Maryland Cavalry, rode to the road that the wagons were traveling upon and ordered the northeast portion of the wagon train to stop, while ordering the westbound portion of the wagon train to hurry down the mountain. General Jones countermanded Emack’s order sending the wagons onward. Jones’ informed Emack that the wagons must remain moving in the direction of Waynesboro. He would have to hold the Union cavalry as long as he could in order to protect the wagon train.

During the battle, Kilpatrick divided his command, sending a small force one mile to Fairfield Gap by way of modern day Furnace Road. This was done in an attempt to sever the Confederate wagon train, charge down from there, destroying all that was in the road, and then hit the right of the Confederate force at Monterey Pass. However, the 1st Michigan, who were tasked with this job were pushed back, never completing their mission. Kilpatrick also sent the 1st Vermont Cavalry from Monterey Pass to Raven Rock Pass, a few miles to the south, in order to attack the head of the wagon train that may have been in Smithsburg. Upon seeing no wagons there, they trotted to Leitersburg where they intersected three miles worth of wagons there, and setting fire to many.

As Kilpatrick divided his command, he sent Custer’s brigade to the front to dislodge the Confederate force that held Monterey Pass. During the final hour of the fight, Kilpatrick managed to get a section of Pennington’s Battery in place to bombard the intersection that the wagons were traveling into. Once the 1st West Virginia Cavalry broke through the Confederate battle line and tumbled the cannon down the embankment, they turned their foremost attention to the prized wagons that massed over the road. Following behind the West Virginians was that of Custer’s brigade.

Union horsemen swung in and out of the Rodes’ portion of the wagon train. Between the lightning and the firing of guns, some of the drivers lost control of their wagons, forcing them to overturn down the steep mountain cliffs. Many Union cavalrymen shot the lead horse in order to get the wagons to come to a halt. Many of these wagons contained ordinances that were used for the artillery and they were set on fire. The fires extended from atop South Mountain at Monterey Pass to the foot of the mountain. As Confederate cavalry reinforcements tried to organize, they could not form a line fast enough before the union cavalry broke through again.

The citizens of Waynesboro knew exactly where the Union cavalry was located by the explosions they saw extending down the mountainside. The town’s residents witnessed such a Fourth of July spectacle, unlike any they would ever witness again. The fires of the wagons in the direction of Leitersburg and Monterey Pass must have been an amazing picture. Just after dawn the smoke rising from Ringgold could be seen.

At the toll house, Pennington’s guns, and from some reports, Elder’s Battery as well, raked fire upon the oncoming wagons that were trying to get to the Emmitsburg and Waynesboro Turnpike. As Confederate reinforcements arrived at the gap, Kilpatrick ordered his reserves down the mountain collecting their bounty until dawn.

The 1st Vermont at Leitersburg would divide their forces, sending some toward Hagerstown, then to Williamsport, and on to Boonsboro. The other half of the 1st Vermont would meet back up with Kilpatrick at Ringgold. The wagons that were taken by Kilpatrick were ordered to halt at Ringgold, where Kilpatrick ordered his men to take inventory of the merchandise. Anything that could be of use to Kilpatrick or the Union army would be separated out. The remaining, unnecessary wagons were to be burned in the fields surrounding Ringgold.

In all, nine miles worth of wagons, ambulances, blacksmith (forge) and battery wagons, around 200 to 250 vehicles total were captured and destroyed during the Battle of Monterey Pass and the affair at Leitersburg. Among the wreckages of the wagons were roughly 900 drivers, teamsters and regimental quartermasters that were wounded or taken prisoner.

Realizing that he was in a dangerous situation, Kilpatrick ordered his cavalry to Smithsburg, a few miles to the south, where he would fight Stuart later in the afternoon and evening. From there Kilpatrick withdrew from the field and arrived near Turner’s Gap just after midnight of July 6th, where he would turn over his spoils to be escorted to Frederick, Maryland. Kilpatrick would again try to intercept the wagons on July 6th with a coordinated effort between himself and General John Buford, but they would be forced to retire in the streets of Hagerstown and at Williamsport.

Images: LOC

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