Meanwhile, Mr. Baer had come into contact with Susan Lookabaugh and told her to get help. She managed to walk by the Confederate pickets and headed toward Fountaindale, where she came in contact with James Embley. Miss Lookabaugh told Mr. Embley about the situation at Monterey Pass and asked him to get help.

Near the hamlet of Fountaindale Charles H. Buhrman, a local farmer received this message from Mr. Embley who told him about the capture of Mr. Baer and Mr. Miller at the Monterey House and about the Confederate retreat on Jacks Mountain. Mr. Buhrman then mounted his horse and traveled toward Emmitsburg looking for any Federal soldiers in area that he could find. He came across one of General Kilpatrick’s scouts two miles below Fountaindale. The pickets escorted Mr. Buhrman to General Custer where he reported what he was told. General Custer then escorted Mr. Buhrman to General Kilpatrick.

Charles H. Buhrman. Image source: Bates' Franklin County History

Near Fountaindale General Kilpatrick was directing his artillery to deploy and begin shelling the Confederates at McMullin's Hill. Mr. Buhrman told General Kilpatrick about the layout of the Confederate forces at Monterey Pass and told him about the cannon planted in the middle of the road at the Clermont House. 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.

As Mr. Buhrman rode with General Kilpatrick, the 1st Michigan Cavalry came across a local 12 year old girl named Hitty Zeilinger, who told them that the Confederates had placed a cannon near the Clermont House on top of the mountain. She knew Mr. Buhrman and begged him to tell General Kilpatrick not to go up to Monterey Pass. One of the 1st Michigan Cavalry soldiers lifted 12-year-old Hitty into his saddle and they traveled up the mountainside together. They soon came to Charles Buhrman’s farm where he told General Kilpatrick that this was as far as he would go. General Kilpatrick asked Mr. Buhrman to continue with him as his scout and Mr. Buhrman agreed.

General Kilpatrick traveled about one mile along Waynesboro Pike, when he came across a Confederate scouting party that belonged to Captain Emack. Using local citizens as guides, Kilpatrick galloped through the rainy evening on a collision course toward the Confederate wagons passing through Monterey. Mr. Miller heard a great deal of movement outside of where he was being held. He remembers "About dusk I saw a great deal of commotion among them and asked some of the soldiers what was going on. "Oh nothing! Just you report to Sergeant Grabill," was the reply. I came to the house and asked Willie Waddell whether he knew what was going on. "Yes," said he, "I just came down from the observatory on the top of the house and could hear the Union troops coming up 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 9:00 pm Custer’s men came in contact with Confederate pickets from Captain George Emack’s company of the Confederate 1st Maryland Cavalry that was stationed near the Clermont House, located one half mile south of Monterey Pass on the Waynesboro-Emmitsburg Pike.

Hearing 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 Tanner 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. The shots were fired over their heads, but managed to get the 5th Michigan’s attention and put fear in their hearts.

Captain Emack ordered the rest of his company to dismount and deploy on both sides of the cannon. Captain Tanner’s men fired two more shots. After the confusion subsided, Captain Emack's company then mounted and charged forcing the 5th Michigan back, where Kilpatrick's Artillery was stationed near McMullin’s Hill. Allowing the 5th Michigan to reorganize before advancing back into the mountain gap, Mr. Buhrman told Kilpatrick to dismount a regiment and send them to the left of the road where they could seize the cannon and possibly out flank Captain Emack’s men. Kilpatrick thought the tactic suggested might work and he ordered the 8th Pennsylvania to dismount and march through the dense stretch of woods toward the Clermont House for the first advance into Monterey Pass. The 8th Pennsylvania Cavalry covered the ground about 100 yards to the left portion where the Clermont house once stood and where Monterey Circle is today.

In a letter to the Valley Spirit in 1886, Charles Buhrman recalled: “It was then getting dark in the evening. After passing Clermont about the rebels fired three or four shots with grape and canister, and then pulled up their battery, and retreated. I don't think they killed any of Kilpatrick's men with the battery, as they fired too soon, and the grape and canister went over our men's heads; but it made some of our men retreat, and caused a great deal of confusion. I told Kilpatrick if he would dismount a regiment and go down through the edge of the woods, he could flank them and capture the battery.”

Seeing that he might be out flanked, Captain Emack withdrew his force about 200 yards past the Monterey House. This gave him time to concentrate his force at the mountain pass. Captain Tanner then ordered to have the cannon be redeployed from its current position and reinforce Captain Emack near the Monterey House where his troopers were ordered to deploy on both sides of the road. This maneuver was carried out in such a hurry that Captain Tanner’s men were forced to leave their caisson behind and members of the 8th Pennsylvania took possession of it.

As the majority of General Kilpatrick’s Cavalry began to ascend the eastern side of the mountain, Kilpatrick saw the conditions of the road as his troops moved westward toward the Monterey House. On his right was Monterey Peak, which was a rough rugged portion of Monterey Pass. To the left was a steep ravine and to his front was a road too narrow to even deploy his artillery. After Captain Emack placed his troops near the Monterey House, Custer’s men consisting of a portion of the 1st and 5th Michigan Cavalry began their advance.

The 5th Michigan was sent toward the right to protect Kilpatrick’s right flank. A small portion of the 1st Michigan Cavalry was ordered to dismount and continue on the main road. This forced Captain Emack to slowly fall back further westward until the Custer’s Brigade gained the eastern half of Monterey. This forced Captain Emack to withdraw his force even further back to eastern side of the Maria Furnace Road where it connected to the Emmitsburg and Waynesboro Turnpike.

General Kilpatrick stopped at the Monterey House where David Miller and Jacob Baer were held prisoner. He dismounted and walked up on the porch where Mr. Miller and Mr. Baer were. General Kilpatrick started to discuss the roads of the area and where they led when one of General Custer's men came riding up to the Monterey House asking General Kilpatrick for more men. Kilpatrick did not honor General Custer's request for more manpower. Later in life Mr. Baer recalled that General Kilpatrick told the courier to tell General Custer, "He had enough men and lick the hell out of them!”

During the conversation, General Kilpatrick asked David Miller about the roads and where they led. Mr. Miller informed General Kilpatrick of the Mount Zion road that led into Smithsburg and Leitersburg. General Kilpatrick then asked Mr. Miller who he knew that could guide a regiment of his cavalry down the western side of the mountain so they could try and cut off the Confederate wagon train. David Miller saw Charles Burhman talking to some of the Union officers, and he turned to General Kilpatrick and told him that Mr. Buhrman was the man for the job.

General Kilpatrick asked Mr. Buhrman where he thought the wagon train was going. Mr. Buhrman later recalled: “Kilpatrick asked me which way I thought the wagon train was going, and where I supposed they would strike the river. I told him they could go by Smithsburg and Boonsboro, and cross the river at Sharpsburg, or go by Leitersburg and Hagerstown and cross at Williamsport. He asked me if there was any road that I knew of that I could take a regiment and head off that wagon train. I told him there was that I could take them by Mount Zion and then down the Raven Rock Hollow and strike Smithsburg, and if they had not taken that road, we could cross to Leitersburg and there we would strike them for certain.”

General Kilpatrick ordered Lt. Colonel Preston of the 1st Vermont Cavalry to take Mr. Buhrman as his guide and travel through Blue Summit, taking the road leading to Smithsburg. This wooden road took them through modern day Blue Ridge Summit and Cascade to Smithsburg. Upon their arrival at Smithsburg they found that everything was quiet. Mr. Buhrman then told Colonel Preston to take the road leading to Leitersburg that was 4 miles away and by daylight they had captured several prisoners and wagonloads of supplies.

As soon as Colonel Preston and the 1st Vermont Cavalry rode off toward Smithsburg, General Kilpatrick ordered Colonel Town to take a regiment of his battalion to head off the retreating wagon train. Near the Clermont House, the 1st Michigan Cavalry under Lt. Colonel Peter Stagg was sent on a road leading to Fairfield Gap to head off the Confederate wagon train coming out of Fairfield.

General Custer hired Emmitsburg resident James McCullough on June 27th as a guide during the Pennsylvania Campaign, when the Michigan Brigade encamped at the old Toll House south of Emmitsburg. During the battle of Monterey, McCullough guided Colonel Stagg’s 1st Michigan Cavalry to Fairfield Pass.

As all of this was happening at the same hour, General Kilpatrick had made plans of an attack from the east and west which was already underway; he now had to concentrate on gaining the actual pass of Monterey in order to dislodge Captain Emack and his Marylander’s. As the third wave of the battle was underway, Custer’s men began to get disorganized.

After General Kilpatrick’s Cavalry gained Monterey Pass, they continued down the mountainside to Waterloo (present day Rouzerville). After the affair at Waterloo, General Kilpatrick traveled to Ringgold, Maryland 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.

Once General Kilpatrick entered Ringgold, his men were tired and the horses needed rest. A New York Times reporter by the name of E. A. Paul rode with Kilpatrick and saw first hand the condition of Kilpatrick’s men. The men were tired, wet and covered with mud from the battle of Monterey Pass. As the cavalrymen halted at Ringgold, many men were so exhausted that they fell asleep in the saddle. Kilpatrick’s Cavalry had been riding and fighting for almost twenty-four hours without a break.

While General Kilpatrick’s Cavalry was riding toward Ringgold, Maryland, Charles Buhrman and the 1st Vermont Cavalry had already traveled down Mount Zion Road and then took the Raven Rock Hollow and came out to Smithsburg. When they arrived at Smithsburg, not one Confederate soldier was to be found and everything was quiet. Mr. Buhrman thought that maybe the Confederate wagon train had taken the road to Leitersburg. Colonel Preston ordered the 1st Vermont to head toward Leitersburg and they arrived at daybreak finding the road filled with Confederate soldiers, livestock and the wagons that survived the battle of Monterey Pass.

Charles Buhrman later recalled: “The regiment I was with captured a great many prisoners, cattle, horses, etc., and destroyed the wagon train from Leitersburg back to Ringgold. There they met the remainder of Kilpatrick's cavalry. They had destroyed the wagon train from Monterey to Ringgold, a distance of six miles, and from Ringgold to Leitersburg, a distance of three miles more, making nine miles of wagon train captured or burned or destroyed by cutting off wagon tongues and cutting spokes in wheels. I am not able to say how much, if any, of the wagon train was destroyed between Leitersburg and Hagerstown, as I went only as far as Leitersburg with the 1st Vermont regiment, when it divided, part going toward Hagerstown, and part toward Ringgold. I went with the part that went toward Ringgold, as that was on my way home. I left them about 8 o'clock on Sunday morning, and started home by way of Ringgold.”

Charles Buhrman started for home. He rode by himself to Ringgold where he was taken prisoner, by General Kilpatrick’s pickets. As they escorted him to the old school house, Mr. Buhrman explained that he was with Kilpatrick during the battle of Monterey Pass, but the pickets didn’t believe a word Buhrman said. As Buhrman walked into the schoolhouse several of Kilpatrick’s officers recognized him. They ordered Buhrman’s release and he continued toward home. Buhrman took the road leading to George Harbaugh’s farm and as soon as he got up the hill, he saw Confederate soldiers riding down the other side. Avoiding capture by the Confederate soldiers, Buhrman traveled along the foot of the mountain and rode his horse through the woods until he came to Germantown Road near the schoolhouse.

From there he continued to the Sabillasville Road near Monterey Pass where he found Confederate pickets that were guarding the Frederick County, Maryland side. About sixty yards from the Confederate pickets, he was spotted and they called to him to dismount. Unable to jump a high fence near an orchard, Buhrman recalled: “I was near the orchard fence, I "dismounted" over the fence and did some good running from that to the Pine Swamp, about one-fourth of a mile. They shot four times at me, but missed me. I heard the balls whistle over my head, as it was down hill and they shot over me. I lost my horse, saddle and bridle. I was in the swamp only a few minutes until they were there; but as the bushes were very thick, I soon got away from them and kept the woods until I got home, two miles from there. It was then two or three o'clock on Sunday afternoon.”