General Ewell's wagon train was roughly 17 miles long with the
contents of "plunder" gathered during the Gettysburg Campaign, as
a result of liberal rebel foraging from the farms of Pennsylvania.
Five thousand cattle along with a sizable number of free blacks,
confiscated as "contraband" of war, were also part of this column.
General Grumble Jones was assigned the task of guarding General
Richard Ewell’s wagon train and the mountain passes along with the
6th Virginia Cavalry and 50 men of the 1st Maryland Cavalry under
the command of Captain George Emack, whose company took the lead.
Assisting Emack was 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 via Maria Furnace Road.
The head of the wagon column reached Rouzerville late in the
evening of Saturday July 4th, where the Confederates took the Old
Hagerstown Road going along South Mountain toward Smithsburg. The
Confederates learned of the presence of Union forces in that
direction and they immediately turned and started for the road
that led to Ringgold and Leitersburg.
A turn of the Century view of the Fairfield area from
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
worse. The heavy down pours 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.
The town of Waynesboro witnessed the first portion of the
Confederate wagon train that was traveling down the mountain side.
This large wagon train of wounded soldiers traveled from Fairfield
and was conveyed over South Mountain. This must have been a site
to see not to mention the noise it brought as hundreds of wagon
wheels were rolling through town. In addition to the wounded
soldiers it also contained ammunition and supplies of various
General Stuart was given the task of screening the area toward
Thurmont keeping an eye open for any possible attacks from the
Union forces. A portion of Stuart’s Horse Artillery Battalion was
to stay behind at Fairfield. Mooreman’s, Chew’s, and a portion of
McGregor’s batteries were ordered to protect the wagons of General
Ewell’s Corps. Joining them were Robertson’s and Jones’ Cavalry
Brigades. As they marched through Fairfield, the artillery was
ordered to halt a short distance beyond the Oak Grove Inn.
During the afternoon the artillery sat watching General Ewell’s
wagon train moving westward as it traveled the old Iron Springs
Road. This road led over Jacks Mountain and Piney Mountain where
it cleared the South Mountain range. During the wait Mooreman’s
Battery was ordered to move back through Fairfield where it
encountered and drove a unit of Federal Cavalry back. Captain W.
K. Martin Acting Adjutant of Jones’ Cavalry Brigade noted his
regiment was in line of battle, supporting Moorman's battery on
the road leading from Fairfield to Emmitsburg. During this small
fight Gunner George McDonald was using a newly imported double
barrel rifled cannon.
Before darkness, the 2nd Rockbridge Artillery had crossed over
Jacks Mountain. There, on top of the mountain they were ordered by
General Anderson to leave a section of artillery on top of the
Emmitsburg and Waynesboro road. Later that night a portion of the
2nd Rockbridge Artillery was to take position on the hill
overlooking Waynesboro, guarding the wagon train as it continued
down the mountain. General Anderson was to hold the gaps in the
mountains between Fairfield and Waynesboro as he directed his
command to Frogtown, located at the base of the mountain.
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.
Tanner's Battery marched to Fairfield and then onto Monterey Pass.
After arriving at Monterey, Captain Tanner order one
to be deployed, while the other four 3-inch rifles continued westward toward Waterloo. Captain Tanner ordered the
cannon to be deployed at the eastern slope of Monterey Pass facing
the village of Fountain Dale. The men of Tanner's Battery unlimbered the cannon
and limber and waited for further orders. The lone cannon
had only 5 rounds of ammunition in the limber.
Around 6 p.m. the last of General Ewell’s wagon train had
passed by the artillerymen in Fairfield. A cannon from Chew’s
Battery was left behind and eventually used to fire upon the Union
cavalry as it tried to find a weakness in the rear of General
Ewell’s wagon train. The other pieces of Chew’s Battery were to
bring up the rear with Cavalry in support, acting as a rearguard
for General Ewell’s wagons as they continued over Jacks Mountain.
On the morning of July 4, General Kilpatrick’s Cavalry Division
which consisted of General George Custer 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 in pursuit of
General Ewell's command, that was reported as being in the
mountains in the vicinity of Monterey moving on the road between
Fairfield and Waynesboro.
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. 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 toward the mountains. A short distance from
Emmitsburg, the 6th Ohio Regiment of Huey’s command came in
contact with rebel pickets who were driven off. Near the hamlet of
Fountain Dale, 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 that he could find. 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. General Kilpatrick came across a
local girl, who told him that the Confederates had placed a cannon
near the Monterey House on top of the mountain.
At Fountain Dale,
the 1st Michigan Cavalry was sent upon a road leading from the
right of town to Fairfield Gap, where the enemy was found
occupying it. One squadron, under the command of Lieutenant
Colonel Stagg against superior numbers made a successful charge.
The enemy was driven out and the Gap held until the entire column
and train had passed. Here Colonel Stagg sustained heavy losses.
In leading the charge, Colonel Stagg’s horse was killed, and Stagg
himself was seriously injured by the falling horse. Captain
William R. Elliott was also mortally wounded and Lieutenant James
S. McElhenny and 17 men were killed. The 1st Michigan retreated
back into Fountain Dale and met up with General Custer.
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
pm 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 Fountain
Dale, located one mile south of Monterey Pass on the
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
After the confusion subsided, Emack's small squad charged and
drove the Federals down the mountainside, where Kilpatrick's
Artillery was stationed.
Allowing things to calm down a bit, General Kilpatrick and
General Custer reorganized before advancing back into the mountain
gap. This gave Captain Emack time to concentrate his force at the
mountain pass. Orders came to have the cannon to redeploy 100
yards from it's current position and reinforce Captain Emack near the
Monterey House where his troopers were deployed on both sides of
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. Emack later recalled:
"In the mean time the wagons had commenced to run in on the
road in my rear, and I again went back on the Gettysburg road and
stopped them. They were soon started again, and on going back to
ascertain the cause I was informed that they were moving by
General W. E. Jones' orders. I found General Jones and told him
that I had only a handful of men opposed to all of Kilpatrick's
cavalry; and I urged the importance of keeping the road clear, so
that when the enemy broke through he would find nothing on it. The
general said that the train must move on, and if I could hold out
a little longer the 6th Virginia Cavalry would come to my
assistance. I returned to my men and urged them not to yield an
inch nor to waste any ammunition (we had but little at the
In General William E. Jones official report, he stated:
"The evening of July 4th, when it was reported the enemy were
advancing in force on the Emmitsburg and Waynesboro' Road, I saw
that General Ewell's train was in danger, and asked to go with
my command to its protection. I was allowed the 6th and 7th
regiments and Chew's battery; but the 7th was afterwards ordered
back, and Colonel Ferebee's regiment (4th North Carolina
Cavalry) allowed taking its place, the latter being then on this
road. This narrow and difficult way, rendered doubly so by heavy
rain just fallen, was so blocked by wagons as to render it
wholly impracticable to push ahead the artillery or even the
cavalry. With my staff I hastened on to rally all the stragglers
of the train to the support of whatever force might be guarding
the road. Arriving, I found Captain G. M. Emack's company of the
Maryland Cavalry, with one gun, opposed to a whole division of
Federal cavalry, with a full battery. He had already been driven
back within a few hundred yards of the junction of the roads.
Not half of the long train had passed. This brave little band of
heroes was encouraged with the hope of speedy reinforcements,
reminded of the importance of their trust, and exhorted to fight
to the bitter end rather than yield. All my couriers and all
others with firearms were ordered to the front, directed to lie
on the ground and be sparing of their ammunition. The last
charge of grape was expended and the piece sent to the rear. For
more than two hours less than fifty men kept many thousands in
check, and the wagons continued to pass long after the balls
were whistling in their midst."
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 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 spared as the bullet traveled through his hat.
He then fired at the Confederate soldier killing him instantly.
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 ordered
to charge the Confederate cannon, which it did with all the
strength they could muster.
At 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.
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 ordered his couriers and staff officers to get into
the fight. The wounded who could fire a gun was also ordered to
stand and fight.
Seeing Capehart's Cavalry in their front, Captain Tanner
ordered the cannon to fire it's 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.
A turn of the Century view of
Monterey. This is where the 2nd attack took place. The old
Monterey House stood to the right.
As mayhem ensued, both forces fought, leaving Captain Emack
wounded by shell, shot, and a saber. Captain Emack and General
Jones had to fall back leaving Custer’s men to clear the pass and the 1st West Virginia Cavalry under the command of Major Charles
E. Capehart charged down the other half of the mountain where it
found parts of General Ewell’s wagon train. Riding behind the
Richmond’s Brigade was General Custer’s Brigade of Michigan
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
abandoned the fight at Monterey Pass as Confederate reinforcements arrived.
During the battle of Monterey Pass one of the wagon drivers of
the Richmond Howitzers was captured by the enemy. Sam Liggon, who
was an unarmed wagoneer of the Richmond Howitzers was confronted
by a cavalryman who had his saber drawn and demanded his
surrender. Sam asked him what unit he belonged to and the reply
was the First Virginia. Sam, thinking it was part of his own
command then asked him what was the matter and why was he pointing
a saber at him. The cavalryman then replied he was from the 1st
Virginia of the United States Army. Sam Liggon was forced to yield
and stopped the wagon before it was completely surrounded by the
1st (West) Virginia Cavalry.
Union General Judson Kilpatrick thought he was facing more
Confederates at Monterey Pass than the mere handful that held off
his three Union brigades. The Confederate 1st Maryland Cavalry,
with only one cannon and 20 men, held off 7,000 Union troopers for
over five hours. The Confederates created so much confusion among
the Union ranks that at one point, Emack recalled "the shouting
and firing among the retreating enemy we concluded that they had
become panic-stricken and were accidentally fighting among
Union soldiers wrote about their experiences during the battle
of Monterey. Kilpatrick stated that they brushed away a force of
Cavalry from their front; probably Robertson's picket, but was
afterwards attacked, both in front and rear, on a rugged mountain
side, where the road was too narrow even to reverse a gun.
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 mountain elevation was so high that troops on both sides
could see the stars and hear the roar of the rain and thunder, as
lightning flashed below them. Captain Henry Kidd of Custer’s
brigade stated "It seemed as if the infringement were an immense
tank. The contents of which were spilled all at once, such a
drenching we had! Even heavy gum coats and horsehide boots were
hardly proof against it." Captain Kidd continues "It poured and
poured, making of every rivulet a river and of every river and
mountain stream a raging flood. Many rebels gave themselves up,
being heartily tired of this useless war."
General Bradley T. Johnson, commanding the Maryland Line later
wrote about the battle of Monterey;
"Meade detached Kilpatrick’s division down through Maryland
to strike Lee’s trains in the mountains, and at midnight it
attacked them at Monterey, on the dividing line between Maryland
and Pennsylvania—Mason and Dixon’s line. Emack’s and Welsh’s
squadrons were at the point of attack. They were thrown behind
the stone fences, part held mounted, and as Kilpatrick’s advance
charged in the pitch dark, the Marylanders sent them whirling
back, and charged them mounted. These two squadrons held back
Kilpatrick’s division from midnight until dawn, when Jenkins got
up, it having been impossible to pass the wagon train in the
dark. They saved Ewell’s train, his ammunition and his
ambulances with his wounded."
The action of Monterey Pass was so intense that the citizens of
the town of Waynesboro had not yet been sure of the result of the
battle of Gettysburg. When they saw the fires extending from the
top of the mountain all the way down to Leitersburg, great
excitement prevailed that night. The ammunition wagons were set on
fire, they beheld fireworks and they heard explosions of which no
Independence Day celebration has given them before or since.
As the battle of Monterey was just beginning Chew’s Battery was
moving from Fairfield. Private Charles McVicar of Chew’s Battery
mentioned that heavy rain made traveling impossible crossing
through the mountain gap near Monterey. He could hear the roar of
cannon fire in the distance about 2 1/2 half miles away. He also
noted that the sharpshooters were very hard at work. The firing
was very rapid as daylight was nearing. The road was littered with
wagons of the dead and wounded from the battle the day before.
They managed to find a place for one gun to be unlimbered and
fired a few shots at Federal soldiers. The Federals fell back
afterwards but not before cutting down a few more wagons. The
federals took up positions on the heights. Private McVicar noted
that his gun was supported by two regiments of infantry and threw
up breastworks within an hour. The firing was constant and it was
a night of horror that he would never forget.
Gunner Neese of Chew’s Battery explained what happened to his
unit during the night while they traveled over the road toward
Monterey. Before daybreak on the fifth, the 6th Virginia Cavalry
under the command of Captain John A. Throckmorton came running
down the mountainside. Captain Chew asked the Captain what was
going on and that he had been sent to support him. The Captain
replied that his command had been fired on by Union Artillery and
that the 6th Virginia would not go back until daylight. Captain
Chew was never given the opportunity to support the 6th Virginia
as ordered. They went back down the mountain where they waited for
Located somewhere behind Chew’s Battery, Pegram’s Artillery
Battalion of Pender’s Division of Hill’s Corps began its march
back to Virginia. Drivers of the caissons from this Battalion
whipped their teams of horses trying to keep moving so they
wouldn’t sink down into the mud. Many horses had to be abandoned
along the roadside near Monterey. The wounded men had it worse,
their cries were eventually silenced being overshadowed by the
thunder that cracked echoing throughout the valley.
John Marye of the Fredericksburg Battery (Part of Pegram’s
Artillery Battalion) remembered "Never shall I forget that night’s
march." He continued "Their cries and appeals to their comrades to
leave them by the roadside or else to shoot them and end their
misery, ring in my ears to this day." Many of the enlisted men of
Pegram’s Battalion who had been wounded at Gettysburg traveled
back to Virginia in ammunition wagons that crossed the mountain at
Monterey. Their bodies were jolted with every movement of the
wagon which made the pain of their injuries even worse.
General Wright moved from Gettysburg to Fairfield at around
dark. Because of the downpour it was midnight before he arrived in
Fairfield. The general was handed orders and told to move on to
Monterey Gap to support Iverson’s Brigade that was under attack
from the Union Cavalry. At dawn, General Wright came upon the rear
of the train but found the road completely blocked, making further
progress impossible. He halted his men and permitted them to take
a rest in the mud, while he went to find Iverson. The latter
assured him that the danger was past. Wright directed him to move
on toward Waynesboro while he held the pass.
General Wright later recalled:
"About daylight, I came upon the rear of the train upon the
top of the mountain, but found the road so completely blocked up
as to prevent my farther progress. I halted my command, and
permitted the men to lie down and take a little rest, while I
rode to the front, to ascertain the exact condition of affairs.
I found General Iverson near Monterey, and not far from the
Waynesborough turnpike, and from his learned that all the danger
to the train had passed, and I directed him to move on in the
direction of Waynesborough as rapidly as possible, so as to
enable our troops to get through the mountain pass."
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.
The Powhatan and Salem Artillery had also suffered a great
loss at Waterloo. Because of the lack of ammunition for their
cannon, the Salem and Powhatan Artillery was forced to keep
marching, trying to avoid capture by General Custer's Brigade.
Captain Griffin reported that all of his company's belongings
including tents, forages, ovens, books and papers had all been
captured or destroyed. Because of this he wasn't able to make a
quarterly return for the quarter for all of his losses.
The Fluvanna Artillery’s wagons were also among those destroyed
at Waterloo early on the morning of the 5th. Twenty-five of their
wagoneers were also captured. The Fluvanna Artillery had begun
their march to Virginia on the morning of the sixth. Their wagons
were sent ahead with General Ewell’s wagon train. Sergeant Pettit
describes the scene in Waterloo; "The wrecks of our wagons
captured yesterday, were scattered from the top to the foot of the
mountain. About 50 were captured some carried off, others
destroyed." Many of the men’s spare clothing, personal
possessions, and supplies were in those wagons that were
Second and Third Companies of the Richmond Howitzers belonging
to Captain Willis Dances Artillery Battalion, Rhode’s Division of
General Ewell Corps began their march toward Virginia around 2 a.
m. on July 5th. 2nd Company Richmond Howitzers entered Fairfield,
as an enemy force emerged in the rear of the column, but they were
driven off. Meanwhile, 3rd Company had only gone two miles and by
daylight the rain had stopped. The men were cold and their
uniforms were drenched. 3rd Company managed to get a hold of some
whiskey to keep warm that belonged to 2nd Company. The news of the
battle of Monterey Pass must have been one of sorrow as their
wagons, ambulances, supplies, and many of their sick and wounded
had been captured the day before. Some of their comrades were
never seen or heard of again.
As the 1st Richmond Howitzers, belonging to Colonel Henry
Cabell’s Artillery Battalion, Mclaw’s Division of Longstreet Corps
began it’s withdraw from the blood soaked fields of Gettysburg,
they saw first hand the damaged afflicted by the Federal Cavalry
under General Kilpatrick during the battle of Monterey Pass. 1st
Company had encamped at Monterey Pass on the night of July 5th,
during the rainstorm because road conditions made traveling
impossible. Colonel H. C. Cabell, commanding his Confederate
Artillery Battalion wrote: "During the night of the 4th, we
withdrew from our position, and, after a most distressing march,
encamped at Monterey Springs the night of the 5th."
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 was 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.
Today a historical marker is situated where the wagon train was
captured. It reads: "Brown Springs. During Lee’s Retreat. General
Judson Kilpatrick U.S.A. took 1500 prisoners and 9 miles wagon
train near here."
Today the original roads are still intact, but are on private
property. It has been rumored that Confederate soldiers are still
buried under modern day Route 16 near the intersection of Old
Waynesboro Pike in Monterey. Stories of buried cannon seem to
capture our imagination. One story that comes to mind tells of how
the Confederates hid a cannon in an old cave off of the original
road on what is now called Pennersville Road. Another story states
that a cannon was thrown down a well. Yet there is another story
about a cannon being buried in a field somewhere near Monterey
Lane. The only piece of evidence I have is by Major M. W. Henry
who wrote in his official report: "On July 5th we were still
marching, at 2 p.m. we took up camp on the South Mountain (near
Monterey). The 6-pounder and 12-pounder howitzers, having merely
the gun-carriage attached, were abandoned necessarily for the want
of the proper means of transportation." The Battle of Monterey is
one of the great forgotten battles of the Civil War, let us not
abandon the history of this great battle as this cannon is rumored
Read Part 5