Picketing the Catoctin Mountain and the Fight North of Frederick

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.”

The Fight at Quebec Schoolhouse, A Consequence of the Braddock’s Gap Skirmish

As portions of Confederate General Wade Hampton’s Brigade withdrew through the streets of Middletown during the late afternoon of September 13th, 1862, the skirmish that developed at Braddock’s Gap was finally dying down. General JEB Stuart ordered General Wade Hampton to take the cavalry supply wagons to Burkittsville as quickly as possible, which was about five miles away to the south. From there, General Hampton could join up with Colonel Thomas Munford, who was guarding the approach to Crampton’s Gap. General JEB Stuart himself, along with Hart’s battery, and the Jeff Davis Legion made their way to Turner’s Gap upon South Mountain where General Daniel H. Hill had an infantry brigade deployed, ready to defend the gap.

Upon arriving at Turner’s Gap, General Stuart’s cavalry commanded the National Road forcing Colonel Alfred Colquitt’s brigade to move along side of the road. It was reported that a few brigades of Union infantry had broken through the Catoctin Mountain and were situated in the Middletown Valley. From there Stuart continued onward toward Boonsboro. What Stuart didn’t know was that the rest of Union General Jesse Reno’s Ninth Corps, soon followed by General Joseph Hooker’s First Corps, were in route to Middletown.

After the Confederate cavalry had withdrew from Middletown, portions of Union Colonel John F. Farnsworth’s cavalry brigade had pushed through Middletown to the Catoctin Creek, where the rear of Stuart’s forces had set fire to the covered bridge. It looked as if the tired Union troopers were finally going to have a rest after a hard days’ fight. While the pursuit was still going strong through Middletown, several citizens of Middletown informed Major William Medill of the Eighth Illinois Cavalry about a Confederate wagon train that had just left town moments before their arrival.

As Major Medill tried gathering troops to go after the baggage train, time ticked on and the wagon train advanced further out of their grasp. Major Medill managed to get two companies, A & G of the Eighth Illinois, and two companies, E & F of the Third Indiana, totaling about 230 troopers. William Pickerill of the Third Indiana recalled: “As the cavalry dashed into Middletown two companies of the Eighth Illinois and two companies of the Third Indiana, E and F, were detached and directed to pursue a rebel wagon train, which the citizens of the town told us had gone southward down the valley.”

Finding the wagons wasn’t going to be an easy task. As stated in my article “The Union Soldier during the Maryland Campaign,” weather conditions proved extreme from the heat on the march toward Frederick to a cold front that had pushed through producing rain. With the ground still being damp, no dust would be kicked up by the wagons; therefore their location could not be seen in the distance.

William Pickerill described the Middletown Valley as his unit moved on toward Burkittsville. “We were in the midst of its most fertile farms. Fields of ripening, waving corn were on every hand. Orchards were the background of many a cottage with its shrubbery-bedecked lawn. In the distance were the mountain crests wreathed in the blue haze of a perfect Autumn day’s loveliest sunshine.”

As the Union troopers pressed on, General Hampton found a road paralleling the main the route to Burkittsville. Hampton later recalled: “On the road to this place I discovered, on a road parallel to the one on which we were, a regiment of Yankee cavalry.” The Union cavalry had been spotted. William Pickerill also remembered seeing the wagon train as well. He later wrote “This detachment after a hot pursuit came in sight of the wagon train as it was slowly winding its way up a mountain road, but in its rear was a battery of brass guns and enough rebel cavalry to have swallowed the pursuing force.” These bronze guns were that of Chew’s Battery guarding the rear of the wagon train.

Pickerill continued “The detachment was satisfied with observation and decided that it did not want that wagon train anyhow, and started to return to the command which it had left at Middletown by a short cut down a winding stony ravine, hemmed in on either side by a very crooked worm fence, so that this particular route answered for the channel of a stream and a country road at the same time.”

What the Union cavalry did not realize was that General Hampton detached Cobb’s Legion of cavalry commanded by Colonel Pierce M.B. Young to pursue them. At a little schoolhouse called Quebec, Saturday classes were in session. The children and the teacher would soon witness something they would never forget.

Cobb’s Legion had taken cover in the brush to conceal themselves along the main road to Burkittsville, lying in wait. William N. Pickerill recalled “Quebeck schoolhouse stood at the head of this ravine, and just as Company F of the Third Indiana, the rear company of the detachment, had entered the ravine Cobb’s Legion of rebel cavalry, commanded by Col. P.M.B. Young, dashed down the mountainside past the schoolhouse, charging us with sabers and pistols, and for a few minutes a desperate little cavalry battle ensued.”

As the Union cavalry appeared, Colonel Young’s men waited. As soon as the Union soldiers had passed, Cobb’s Legion charged after and surprised them. After wheeling, Young had come in from the south while Captain Gilbert Wright’s company attacked from the north. Hampton later wrote: “I directed Lieut. Col. Young to charge this regiment. The order was carried out in gallant style.” The Union cavalry responded firing into the Confederate horsemen. Company F of the Third Indiana, the last unit in the column was trapped in a ditch when Cobb’s Legion charged.

Pickerill recalled “The column halted and fired an oblique volley into the charging rebels and then the clash came and Yankees and rebels, horsed and unhorsed, mingled, indiscriminately shooting at each other and using their sabers in the same reckless manner, until the men at the head of the column tore down the fence on the side of the ravine next to the attacking force and went at them in such splendid style.”

During the first few seconds of the fight, over two hundred carbines were discharged and the scene became wild as men fought desperately to get out with their lives, while Young’s men screamed for their surrender. Captain Gilbert Wright of Cobb’s Legion recalled “Give ’em hell, boys” as he succumbed to injury. The legion crossed sabers with the Union cavalry, and as several accounts state sabers were used rather freely. The accounts of saber wounds are listed on several of the muster rolls of those injured. Some of the troopers were killed when sabers smashed the skulls of their opponents.

Fearing that he might be separated from Hampton’s and Munford’s forces, Cobb’s Legion called off the engagement and pulled back leaving their dead and wounded in the hands of the Union cavalry. Hampton stated that he had four killed and nine wounded in the fight at Quebec Schoolhouse. Among the Confederate wounded was Colonel Young. Hampton also wrote that the Union casualties were thirty killed and wounded, and five prisoners taken.

After the fight, the Union cavalry moved back to Middletown, bivouacking under the stars. The Union cavalry had a hard day of fighting both at Braddock’s Gap and Quebec Schoolhouse. The Union cavalry had secured the way for the Union infantry and by morning, the sounds of cannon and infantry musketry would echo throughout the Middletown Valley, as the Union infantry advanced on South Mountain. This would change the war both socially and politically, and force Lee to issue orders for his army to concentrate at Sharpsburg.

The Skirmish of Braddock’s Gap on Catoctin Mountain

During the Maryland Campaign of 1862, many cavalry skirmishes were fought in Frederick County as a result of the Confederate army leaving Frederick, or occupying areas in the Middletown Valley. While the main Confederate army would march over the Catoctin Mountain at Braddock’s Gap (also known as Fairview Pass), detachments of Confederate cavalry would picket several roads that led into the Middletown Valley. One such pass was that of Hamburg, located near the Frederick City Watershed and Gambrill State Park. Hamburg overlooked the area north of Frederick, keeping an eye on Union General Alfred Pleasanton’s cavalry division and their movements.

During the night of September 12th, 1862, as the rear of the Confederate army marched toward Middletown, to concentrate their forces in the Cumberland Valley, the Jeff Davis Legion was left to guard Braddock’s Gap. The Mississippians were under the command of Lieutenant Colonel William T. Martin who was ordered to picket the National Road, keeping an eye on Union troop movements that may come from the direction of Frederick.

During the evening of September 12th, Confederate Captain James F. Hart, commanding the Washington (South Carolina) Artillery was ordered to send two of the Blakely Rifles from his battery to support the Jeff Davis Legion picketing the Catoctin Mountain at Braddock’ Gap. Before daylight on September 13th, Captain Hart deployed his section across the National Road commanding the gap.

General Pleasanton was ordered by General George McClellan to locate the Confederate army by sending his division in several different directions to the south, north, and west to locate the rear of the Confederate army. Union General Alfred Pleasanton ordered Colonel John Franklin Farnsworth’s Second Brigade of cavalry and three batteries to scout the Middletown Valley and South Mountain.

Just after daylight, the Confederates guarding Braddock’s Gap opened fire on the Union cavalry. The Third Indiana cavalry was leading the advance, followed by the Eighth Illinois Cavalry, the First Massachusetts Cavalry, and the Eighth Pennsylvania Cavalry. Captain Casper Crowninshield of the First Massachusetts Cavalry ordered his men to dismount and they quickly lowered themselves to the ground while holding the reins. The sporadic artillery fire sent shells every which way.

Captain Hart’s section fired upon the Union advance pushing them further back and forcing them to reorganize their advancing lines. As skirmishing broke out, the Jeff Davis Legion began to push the Union advance back, but only temporally. The Union troopers deployed on both sides of the National Road and attempted to advance on the mountain gap.

Soon, an order came to have a section from Captain James Madison Robertson’s and Lieutenant Peter Conover Hains’ batteries to deploy and return fire. Colonel Farnsworth then ordered some squadrons of the Eighth Illinois and Third Indiana to dismount as skirmishers and go up the mountain. Lieutenant Hains’ later recalled: “Brought forward the leading section and placed it in action on the right of the road. The other section was held in reserve. Captain Robertson took position on my left and somewhat nearer the enemy. The firing was thus kept up for some time.”

The fight became very hot as both sides were actively engaged for several hours. Union Lieutenant Hains’: “Being under Captain Robertson’s orders, I received orders from him to bring forward my reserved section and open fire. This section I placed in an orchard about 1,400 yards from the enemy. The other section was moved up closer on the right. The whole battery then opened a fire of case-shot and percussion-shell on the enemy, and after a sharp cannonade of several hours the enemy retired.”

During the afternoon, a brisk artillery fire was kept up by Captain Hart’s guns. Lieutenant Colonel Martin received additional reinforcements from Middletown. The First North Carolina Cavalry under the command of Colonel Lawrence S. Baker was the rear guard for their brigade. The troopers formed their lines next to the Jeff Davis Legion, and in a sharpshooter manner, the troopers became hotly engaged with the Union troops where they fought with “perfect satisfaction.” General JEB Stuart later wrote: “They were exposed to a severe fire of artillery and musketry, which they bore without flinching, nor was there the slightest confusion in the ranks.”

General Wade Hampton later wrote: “I beg to commend the conduct of Lieutenant-Colonel Martin and his command while he held the gap of the mountain. The men of Lieutenant-Colonel Martin fought with their accustomed gallantry, and they were able supported by a portion of the North Carolina Regiment, who had been detailed as sharpshooters. Lieutenant-Colonel Martin on this occasion, as on all others, conducted himself as a gallant and able officer.”

During the climax, the Union troopers were held in check until the arrival of two brigades of Union infantry. General JEB Stuart later wrote: “Which was the only force we were yet able to discover, so well did he keep his troops concealed.” Earlier in the day, General Ambrose Burnside received a message from General Pleasanton asking for additional support from the infantry. General Burnside detached a portion of General Isaac P. Rodman’s Division of General Jesse Reno’s Ninth Corps to Braddock’s Gap.

William N. Pickerell of the 3rd Indiana Cavalry recalled the moments before the Union break through of Braddock’s Gap: “Counted off by fours and the dismounted men crawled up the mountainside through bushes and over stone fences, and soon made it too hot for that battery to operate. In this fight Oliver H. Trestor, of Company D, was killed as he leaped a stone wall right into a bunch of Confederates in hiding behind it. The Confederate battery with its supporting cavalry limbered to the rear and broke into a wild flight down the National Road across the Middletown Valley pursued by the Third Indiana and Eighth Illinois into the village of Middletown”.

After a severe cannonading and several warm volleys with carbines, Lieutenant Hains’ stated: “Notwithstanding the inequality of position of our battery and that of the enemy, we drove them from their position with the loss of only two horses.” The Jeff Davis Legion began to fall back, having previously barricaded the road in several places. Captain Hart limbered up his guns, withdrew from Braddock’s Gap, and redeployed on the National Road, waiting for the Union troopers to appear. Lieutenant Hains’ recalled: “Upon their retiring, we followed with alacrity, and overtook them again near Middletown.”

As the Union cavalry began their decent down the Catoctin Mountain, trooper Pickerall recalled, “Encircled with forest crowned mountain ranges, I have seen no lovelier landscapes than the Middletown Valley, as it appeared to me.” Charles M. Smith of the 1st Massachusetts Cavalry recalled: “Abandoned Confederate corpses lying motionless along the roadside and adjacent cornfields haunted me.”

Union Captain Horatio G. Gibson’s Battery then came up, and “soon in beautiful style induced another backward movement.” Farnsworth’s Brigade then advanced, and engaged the cavalry until they were driven beyond Middletown about 1,000 yards, to a third position. A few rounds fired from a section of Hains’ Battery positioned on the left, and Gibson’s Battery that was deployed on the right, “sufficed to silence” the Confederate Blakely rifles of Captain Hart’s Battery.

Buying enough time for the Confederate army, those Confederates engaged at Braddock’s Gap were ordered to withdraw to Boonsboro. General Pleasanton later wrote: “The Confederates retreated rapidly to Turner’s Gap of the South Mountain; but before doing so they blew up the bridge on the Catoctin Creek, and set fire to the barn and other valuables of the persons residing at that point.”

As Braddock’s Gap was overwhelmed by the Union cavalry, General Burnside ordered the rest of General Reno’s Ninth Corps to move at once to Middletown. After the Confederate cavalry retired, portions of Colonel Farnsworth’s brigade forded the Catoctin Creek and held the ground securing it for the Union infantry advance. Lieutenant Hains’ positioned one section of his battery on the National Road where he was supported by three squadrons of the First Massachusetts Cavalry. The fighting soon died down as daylight gave way to darkness. As Confederate Daniel H. Hill stood at the opening of Turner’s Gap, he knew by daylight of the 14th, a major battle would soon erupt.

The skirmishing that occurred on September 13th, 1862 set the stage for the Battle of South Mountain. While not a lot of information is known about the Braddock’s Gap skirmish, it was an important part of the Maryland Campaign. Because of this skirmish, it allowed portions of the Union army to march toward Middletown after it was discovered that the majority of the Confederate army was west of South Mountain. The Union army was now a day behind the main Confederate army and the focus would now shift toward South Mountain. It would be up to those Confederate defenders at South Mountain to hold back the Union tide and buy the Confederate army the time that it needed until it could reunite after the fall of Harper’s Ferry on the ground of Lee’s choosing.

Postcards courtesy of USGW Archives