General Grumble Jones volunteered for the task of guarding General Richard Ewell's wagon train as it traveled through the mountain pass of Monterey. Under his command, General Jones had 50 men from Captain George Emack's 1st Maryland Cavalry, Company B who took the lead and the 6th Virginia Cavalry. Assisting Emack were portions of Pogue's and Carter's batteries, who were serving as couriers or scouts. Through the driving rain, General Ewell's wagon train rumbled out of Fairfield traveling toward Jack's Mountain, taking a portion of Iron Springs Road, then through Monterey Pass by way of Maria Furnace Road.

As the daylight gave way to darkness, the mountain proved to be deadly as wagons fell from the cliffs due to the flashes of lightning that almost blinded the horses and their drivers. It started to rain in torrents and the roads became almost impassable as the rain had caused the roads to become badly torn up. At some places flooded streams crossed the road making the conditions even worse. The heavy downpours caused many of the fatigued horse and mule teams to stall or drop dead in the middle of the road, creating traffic jams. The Confederate Artillery floundered through the mud as wagons with broken axles were abandoned, along with broken ambulances filled with the wounded.

Courtney's Artillery commanded by Captain William Tanner was instructed to march to Williamsport with General Imboden's column. Instead, Tanner's Battery reached the Emmitsburg Road, south of Gettysburg sometime during the day, while Imboden was preparing to march his wagon train from Cashtown. Because of this Tanner's Battery marched to Fairfield and then on to Monterey Pass.

The View of Tanner's piece of a artillery facing toward Fountaindale

After arriving at Monterey, Captain Tanner ordered one Napoleon cannon to be deployed while the other three artillery pieces continued westward toward Waterloo. Captain Tanner ordered the cannon to be deployed at the eastern slope of Monterey Pass facing the village of Fountaindale. The men of Tanner's Battery unlimbered the cannon and caisson and waited for further orders. The lone cannon had only 5 rounds of ammunition in the caisson.

On the morning of July 4, General Kilpatrick's Cavalry Division, which consisted of General George Custer's and Colonel Nathaniel Richmond's Brigades were ordered from Gettysburg to attack the trains that were moving on the road between Fairfield and Waynesboro. Around 12 p.m. Colonel Huey arrived at Emmitsburg where he met with General Merritt. Colonel Huey then received orders to report to General Kilpatrick, who was now in pursuit of the wagon train.

General Kilpatrick's men rode into Emmitsburg at a full charge, hoping to find parts of the Confederate Cavalry in town. They were immediately disappointed, as they found no enemy within the town. General Kilpatrick reached Emmitsburg at three o'clock in the afternoon. Kilpatrick was then reinforced by Huey's Brigade from General Gregg's Second Calvary Division along with the 2nd U.S. Battery M of the Horse Artillery belonging to Captain John Tidball's Brigade.

After leaving Emmitsburg with three brigades and a battery, Kilpatrick continued his march toward the mountains. A short distance from Emmitsburg, the 6th Ohio Regiment of Huey's command came in contact with Rebel pickets. These pickets were soon driven off by Huey's command. Near the hamlet of Fountaindale, C. H. Buhrman, a local farmer learned of the Confederate retreat upon Jacks Mountain. He then mounted his horse and traveled toward Emmitsburg looking for any Federal soldiers in area. He came across one of General Kilpatrick's scouts and reported what he had overheard.

When General Kilpatrick learned of the movement of the Confederate Cavalry only five miles away at Monterey Pass, he immediately began to pursue the Confederate wagon train. General Kilpatrick traveled about three miles along Waynesboro Pike, when he came across a Confederate scouting party belonging to Captain Emack. Using local citizens as guides, Kilpatrick galloped through the rainy night on a collision course toward the Confederate wagons passing through Monterey. One of these local citizens was a girl who told General Kilpatrick that the Confederates had placed a cannon near the Monterey House on top of the mountain.

It was about sundown when General Custer's Brigade was at the base of the mountain. The 5th Michigan was the first of Kilpatrick's Cavalry Division to climb the mountain. At around 9 p.m. Custer's men under the command of General Kilpatrick came in contact with Confederate pickets from Captain George Emack's company of 1st Maryland Cavalry that were stationed near Fountaindale, located one mile south of Monterey Pass on the Waynesboro-Emmitsburg Pike.

Hearing reports of General Kilpatrick's movements, Captain Tanner ordered the cannon to be loaded while General Custer's men approached Emack's position. As the weather conditions worsened, the Federal soldiers failed to recognize the Confederate pickets who were wearing black gum blankets over their uniforms. Without making any demonstration, using their bodies to shield the gun, Captain Emack ordered the cannon to fire. The first shot was fired directly into the head of the 5th Michigan Cavalry, causing confusion and chaos in the ranks of the Cavalrymen. Two more shots were fired by Captain Tanner's men. After the confusion subsided, Emack's small squad charged and drove the Federals down the mountainside, where Kilpatrick's Artillery was stationed.

General Custer's brigade reorganized before advancing back up the mountain. This gave Captain Emack time to concentrate his entire force at the mountain pass. Orders came to have the cannon redeploy 100 yards from its current position and reinforce Captain Emack near the Monterey House where his troopers were positioned on both sides of the road. Meanwhile, Captain Emack had rode back toward the road that the wagons were on trying desperately to get them moving as fast as they could, while struggling to get the other half of the wagon train that was approaching the pass to stop.

It was during this time that the 6th Michigan Cavalry regiment was ordered to deploy as skirmishers on both sides of the road during the attack on Monterey Pass. For the next several hours in the rain and darkness, the opposing forces engaged in some of the most confusing and chaotic fighting of the Civil War. In some instances, the soldiers could only tell where the enemy was by flashes of the muzzle from their guns, the cannons or lightning in the sky that illuminated their positions. During the 6th Michigan's line of battle, Sergeant Elliot Norton was surprised by a rebel officer who leaped from behind a tree and fired his revolver. Sergeant Norton's life was miraculously spared as the bullet traveled through his hat. He then fired at the Confederate soldier killing him instantly.

Near the Monterey House, General Kilpatrick deployed his Artillery and shelled the Confederate wagons. By 3:00 a.m., along a creek just west of the Monterey House, Custer's men, supported by Artillery, dismounted and attacked Captain Emack who was reinforced by General Jones near the Tollgate house. Fighting then raged in the woods near the modern day intersection of Route 16 and Charmain Road, leaving Captain Emack wounded by shell, shot, and a saber. Captain Emack was finally reinforced by the 6th Virginia Cavalry and the 4th North Carolina Cavalry as Custer's men approached the actual pass. During the thickest of the fight, General Jones even ordered his couriers and staff officers to get into the fight as well as the wounded that could fire a gun.

The 5th Michigan Cavalry was ordered to dismount, leaving the 1st and the 7th Michigan in reserve to charge the Confederate Battery. Custer was also supported by Battery M, 2nd U.S. Artillery and the 6th Ohio Cavalry until they were ordered to Emmitsburg. While Custer was rallying his men, a bullet struck his horse. It was at this time that the 1st West Virginia Cavalry was then ordered to charge the Confederate cannon, which it did with all the strength they could muster.

Seeing Richmond's and Custer's Cavalry in their front, Captain Tanner ordered the cannon to fire its last two shots before the gun was flanked from both sides. Captain Tanner and his crew retreated through the mountain pass and proceeded down the mountainside until they came to Waterloo. One of Captain Tanner's men, Private Thomas Haskins was taken prisoner during the Federal flanking movement on the cannon.

Custer's Cavalry soon cleared the pass allowing Major Charles E. Capehart to charge through the mountain pass. Riding behind the Richmond's Brigade was Custer's Brigade. Custer and his troopers finally caught up to the wagon train and immediately began capturing wagons and prisoners, storming through the long line of wagons, collecting their bounty until dawn. Kilpatrick's Cavalry succeeded in capturing and destroying a large number of wagons, and took 1,360 Confederate soldiers as prisoners. By the morning of July 5th, General Kilpatrick reluctantly abandoned the fight at Monterey Pass as Confederate reinforcements arrived.

Members of General Custer's brigade spoke of the circumstances that made this midnight battle even worse. Several soldiers told stories relating that "the darkness was so intense that the guns could be of little use, except to make the night terribly hideous. The echoes of which reverberated in the mountain gorges in a most frightful manner. Adding to the horrors, the rain fell in floods soon accompanied by the groaning of thunder, while lightning flashed from cloud to cloud, only to leave friend and foe enveloped in the greater darkness."

The action of Monterey Pass was so intense that the citizens of the town of Waynesboro saw the fires extending from the top of the mountain all the way down to Leitersburg, great excitement and unrest prevailed that night. The ammunition wagons were set on fire, providing fireworks and explosions of which no Independence Day celebration had given them before or since.

After the battle of Monterey Pass, General Kilpatrick's Cavalry continued down the mountainside to Waterloo (present day Rouzerville). There he continued to destroy wagons and capture more Confederate soldiers. The First Rockbridge Artillery had their supply wagons destroyed by Kilpatrick's Cavalry in an engagement at Waterloo. In these wagons were utensils, cooking supplies, food, baggage belonging to their officers, and about 25 men who were sick, wounded, or dying.

After the affair of Waterloo, General Kilpatrick traveled to Ringgold where he ordered his division to halt. The casualties of these battles proved to be devastating for the Confederates. General Kilpatrick stated his losses at Monterey Pass were 1 killed, 12 wounded, and 30 captured. The Confederate official reports state that the Confederates lost more than one thousand men, captured at the battle of Monterey Pass along the Waynesboro and Emmitsburg Road.

The battle of Monterey Pass is one of the little known Civil War battles in our nation's history. Its historical significance includes the fact that it was the second largest battle of the Civil War fought in Pennsylvania and the only battle that was fought in two states and four counties.