Fight at Monterey Pass
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The Fight at Monterey Pass (or Gap) was an American Civil War
American Civil War
The American Civil War was a civil war fought in the United States of America. In response to the election of Abraham Lincoln as President of the United States, 11 southern slave states declared their secession from the United States and formed the Confederate States of America ; the other 25...

 military engagement
Engagement (military)
A military engagement is a combat between two forces, neither larger than a division and not smaller than a company, in which each has an assigned or perceived mission...

 beginning the evening of July 4, 1863, during the Retreat from Gettysburg
Retreat from Gettysburg
The Confederate Army of Northern Virginia began its Retreat from Gettysburg on July 4, 1863. Following General Robert E. Lee's failure to defeat the Union Army at the Battle of Gettysburg , he ordered a retreat through Maryland and over the Potomac River to relative safety in Virginia. The Union...

. A Confederate
Confederate States Army
The Confederate States Army was the army of the Confederate States of America while the Confederacy existed during the American Civil War. On February 8, 1861, delegates from the seven Deep South states which had already declared their secession from the United States of America adopted the...

 wagon train of Lt. Gen. Richard S. Ewell
Richard S. Ewell
Richard Stoddert Ewell was a career United States Army officer and a Confederate general during the American Civil War. He achieved fame as a senior commander under Stonewall Jackson and Robert E...

's Second Corps, Army of Northern Virginia
Second Corps, Army of Northern Virginia
The Second Corps of the Army of Northern Virginia was a military organization within the Confederate Army of Northern Virginia during much of the American Civil War. It was officially created and named following the Battle of Sharpsburg in 1862, but comprised units in a corps organization for quite...

, withdrew after the Battle of Gettysburg
Battle of Gettysburg
The Battle of Gettysburg , was fought July 1–3, 1863, in and around the town of Gettysburg, Pennsylvania. The battle with the largest number of casualties in the American Civil War, it is often described as the war's turning point. Union Maj. Gen. George Gordon Meade's Army of the Potomac...

, and Union
Union Army
The Union Army was the land force that fought for the Union during the American Civil War. It was also known as the Federal Army, the U.S. Army, the Northern Army and the National Army...

 cavalry under Brig. Gen.
Brigadier general (United States)
A brigadier general in the United States Army, Air Force, and Marine Corps, is a one-star general officer, with the pay grade of O-7. Brigadier general ranks above a colonel and below major general. Brigadier general is equivalent to the rank of rear admiral in the other uniformed...

 H. Judson Kilpatrick attacked the retreating Confederate column. After a lengthy delay in which a small detachment of Maryland cavalrymen delayed Kilpatrick's division, the Union cavalrymen captured numerous Confederate prisoners and destroyed hundreds of wagons.

Background

General Robert E. Lee
Robert E. Lee
Robert Edward Lee was a career military officer who is best known for having commanded the Confederate Army of Northern Virginia in the American Civil War....

 ordered his Confederate Army of Northern Virginia
Army of Northern Virginia
The Army of Northern Virginia was the primary military force of the Confederate States of America in the Eastern Theater of the American Civil War, as well as the primary command structure of the Department of Northern Virginia. It was most often arrayed against the Union Army of the Potomac...

 to begin withdrawing from Gettysburg
Gettysburg, Pennsylvania
Gettysburg is a borough that is the county seat, part of the Gettysburg Battlefield, and the eponym for the 1863 Battle of Gettysburg. The town hosts visitors to the Gettysburg National Military Park and has 3 institutions of higher learning: Lutheran Theological Seminary, Gettysburg College, and...

 following his army's defeat on July 3, 1863. When Maj. Gen.
Major general (United States)
In the United States Army, United States Marine Corps, and United States Air Force, major general is a two-star general-officer rank, with the pay grade of O-8. Major general ranks above brigadier general and below lieutenant general...

 George G. Meade's Army of the Potomac
Army of the Potomac
The Army of the Potomac was the major Union Army in the Eastern Theater of the American Civil War.-History:The Army of the Potomac was created in 1861, but was then only the size of a corps . Its nucleus was called the Army of Northeastern Virginia, under Brig. Gen...

 did not counterattack by the evening of July 4, Lee realized that he could accomplish nothing more in his Gettysburg Campaign
Gettysburg Campaign
The Gettysburg Campaign was a series of battles fought in June and July 1863, during the American Civil War. After his victory in the Battle of Chancellorsville, Confederate General Robert E. Lee's Army of Northern Virginia moved north for offensive operations in Maryland and Pennsylvania. The...

 and that he had to return his battered army to Virginia. His ability to supply his army by living off the Pennsylvania countryside was now significantly reduced and the Union could easily bring up additional reinforcements as time passed, whereas he could not. Prior to the movement of the infantry and artillery, however, Lee was concerned with removing his long train of wagons, supplies, and wounded men over South Mountain
South Mountain (Maryland and Pennsylvania)
South Mountain is the northern extension of the Blue Ridge Mountain range in Maryland and Pennsylvania. From the Potomac River near Knoxville, Maryland in the south, to Dillsburg, Pennsylvania in the north, the long range separates the Hagerstown and Cumberland valleys from the Piedmont regions of...

 and into the Cumberland Valley
Cumberland Valley
The Cumberland Valley is a constituent valley of the Great Appalachian Valley and a North American agricultural region within the Atlantic Seaboard watershed in Pennsylvania and Maryland....

. He sent the majority of the wagons and ambulances under the direction of Brig. Gen. John D. Imboden
John D. Imboden
John Daniel Imboden was a lawyer, teacher, Virginia state legislator. During the American Civil War, he was a Confederate cavalry general and partisan fighter...

 over the Chambersburg Pike, which passed through Cashtown
Cashtown-McKnightstown, Pennsylvania
The Cashtown-McKnightstown Census Designated Place was the 2000 United States Census area designated by obsolete Census Code 11588 which has been replaced by the Cashtown and McKnightstown Census Designated Places, which the USGS designated as separate named places on August 30,...

 in the direction of Chambersburg
Chambersburg, Pennsylvania
Chambersburg is a borough in the South Central region of Pennsylvania, United States. It is miles north of Maryland and the Mason-Dixon line and southwest of Harrisburg in the Cumberland Valley, which is part of the Great Appalachian Valley. Chambersburg is the county seat of Franklin County...

 and Hagerstown, Maryland
Hagerstown, Maryland
Hagerstown is a city in northwestern Maryland, United States. It is the county seat of Washington County, and, by many definitions, the largest city in a region known as Western Maryland. The population of Hagerstown city proper at the 2010 census was 39,662, and the population of the...

.

While Imboden's wagons moved northwest, Lee designated a shorter route for his three corps: southwest through Fairfield
Fairfield, Pennsylvania
Fairfield is a borough in Adams County, Pennsylvania, United States. The population was 486 at the 2000 census.-History:During the Gettysburg Campaign in the American Civil War, the Battle of Fairfield played an important role in securing the Fairfield pass and the Hagerstown Road, enabling Robert E...

 and over Monterey Pass
Monterey pass
Monterey Pass is a mountain pass near Blue Ridge Summit, Pennsylvania, and the Mason-Dixon Line. The saddle area lies near between Monterey Peak and . It was the site of the July 1863 Fight at Monterey Pass during the Retreat from Gettysburg.-Gettysburg Campaign:The first military engagement at...

 to Hagerstown. After dark on July 4, Lt. Gen. A.P. Hill's Third Corps
Third Corps, Army of Northern Virginia
The Third Corps of the Army of Northern Virginia was a military organization within the Confederate Army of Northern Virginia during much of the American Civil War. The corps was formed in mid-1863 and served until Lee's surrender April 9, 1865, near the end of the war.-Formation:After the death of...

 headed out onto the Fairfield Road, followed by Lt. Gen. James Longstreet
James Longstreet
James Longstreet was one of the foremost Confederate generals of the American Civil War and the principal subordinate to General Robert E. Lee, who called him his "Old War Horse." He served under Lee as a corps commander for many of the famous battles fought by the Army of Northern Virginia in the...

's First Corps
First Corps, Army of Northern Virginia
The First Corps, Army of Northern Virginia was a military unit fighting for the Confederate States of America in the American Civil War. It was formed in early 1861 and served until the spring of 1865, mostly in the Eastern Theater. The corps was commanded by James Longstreet for much of its...

 and Lt. Gen. Richard S. Ewell
Richard S. Ewell
Richard Stoddert Ewell was a career United States Army officer and a Confederate general during the American Civil War. He achieved fame as a senior commander under Stonewall Jackson and Robert E...

's Second Corps
Second Corps, Army of Northern Virginia
The Second Corps of the Army of Northern Virginia was a military organization within the Confederate Army of Northern Virginia during much of the American Civil War. It was officially created and named following the Battle of Sharpsburg in 1862, but comprised units in a corps organization for quite...

. Lee accompanied Hill at the head of the column. Departing in the dark, Lee had the advantage of getting several hours head start and the route from the west side of the battlefield to Williamsport was about half as long as the ones available to the Army of the Potomac.

However, the first traffic on the Fairfield Road had begun on the evening of July 3, when Ewell, concerned about the logistical challenges of the impending retreat, sent his corps trains and herds of captured cattle ahead of his main body. He divided his wagons into three columns. The first used the Cashtown Gap, the second the Fairfield Gap, and the third the Monterey Pass. The wagons headed for Monterey Pass followed the route of Maj. Gen. George Pickett
George Pickett
George Edward Pickett was a career United States Army officer who became a general in the Confederate States Army during the American Civil War...

's division, which was moving to the rear as escorts for the Union prisoners of war from the battle.

Early on July 4 Meade sent his cavalry to strike the enemy's rear and lines of communication so as to "harass and annoy him as much as possible in his retreat." Eight cavalry brigades took to the field. Col. J. Irvin Gregg
John Irvin Gregg
John Irvin Gregg was a career U.S. Army officer. He fought in the Mexican-American War and during the American Civil War as a general officer in the Union army.-Early life and career:...

's brigade moved toward Cashtown via Hunterstown and the Mummasburg Road, but all of the others moved south of Gettysburg. Brig. Gen. Judson Kilpatrick's cavalry division joined up with the brigade of Col. Pennock Huey
Pennock Huey
Pennock Huey was an officer and cavalry brigade commander in the Union Army during the American Civil War.-Biography:...

 at Emmitsburg, Maryland
Emmitsburg, Maryland
-Demographics:As of the census of 2000, there were 2,290 people, 811 households, and 553 families residing in the town. The population density was 1,992.9 people per square mile . There were 862 housing units at an average density of 750.2 per square mile...

, and they were ordered to locate and destroy "a heavy train of wagons" that had been spotted by a Union signal station
Signal Corps in the American Civil War
The Signal Corps in the American Civil War comprised two organizations: the U.S. Army Signal Corps, which began with the appointment of Major Albert J...

. Assuming that Ewell's corps wagon train was actually the main supply trains for Lee's army, Kilpatrick moved out aggressively at 10 a.m. on July 4, proceeding west on the Waynesboro-Emmitsburg Turnpike toward the village of Fountain Dale (just east of present-day Blue Ridge Summit
Blue Ridge Summit, Pennsylvania
Blue Ridge Summit is an unincorporated community in Franklin County, Pennsylvania, United States, southwest of Gettysburg in the central part of the state, adjoining Pennsylvania's southern border with Maryland. It is less than 3 miles east of Pen Mar, Maryland...

 on Pennsylvania Route 16
Pennsylvania Route 16
Pennsylvania Route 16 is a long east–west state route located in southern Pennsylvania, United States. The western terminus of the route is at U.S. Route 522 in McConnellsburg. The eastern terminus is at the Mason-Dixon Line in Liberty Township, where PA 16 continues into Maryland as...

) and Monterey Pass.

Confederate cavalry commander Maj. Gen. J.E.B. Stuart
J.E.B. Stuart
James Ewell Brown "Jeb" Stuart was a U.S. Army officer from Virginia and a Confederate States Army general during the American Civil War. He was known to his friends as "Jeb", from the initials of his given names. Stuart was a cavalry commander known for his mastery of reconnaissance and the use...

 understood the importance of securing the mountain passes and he assigned the primary responsibility to the cavalry brigades of Brig. Gens. Beverly H. Robertson and William E. "Grumble" Jones
William E. Jones
William Edmondson Jones, known as Grumble Jones, was a planter, a career United States Army officer, and a Confederate cavalry general, killed in the Battle of Piedmont in the American Civil War.-Early life:...

. Recognizing the vulnerability of Ewell's immense wagon train in the narrow Monterey Pass, Jones asked permission from Stuart to use his entire brigade to defend it. Stuart allowed the 6th and 7th Virginia Cavalry regiments and a battery of horse artillery under Capt. Roger Preston Chew to be assigned. The 7th Virginia was soon recalled, replaced by the 4th North Carolina Cavalry of Robertson's Brigade.

Engagement in the Pass

Brig. Gen. George A. Custer, a brigade commander under Kilpatrick, received intelligence from a local civilian that the rear of Ewell's wagon train was approaching a large summer resort hotel named Monterey Springs, which sat atop the Pass. Despite being warned of a Confederate artillery placement ahead, Kilpatrick ordered his entire force to advance. A single 12-pounder Napoleon
Field artillery in the American Civil War
Field artillery in the American Civil War refers to the important artillery weapons, equipment, and practices used by the Artillery branch to support the infantry and cavalry forces in the field. It does not include siege artillery, use of artillery in fixed fortifications, or coastal or naval...

 of Courtney's Battery fired a shot at the Union horsemen, but the gunners withdrew before they could be attacked.

The remaining Confederate force on the road up the hill to the Pass consisted of a detachment of 20 dismounted cavalrymen under Capt. George M. Emack from the 1st Maryland Cavalry Battalion, along with a single cannon. As Union troopers from the 5th Michigan Cavalry approached Emack's men, the cannon opened fire and eight of the Marylanders conducted a mounted charge into the head of the Union column. In the dark and the heavy rain, the Union cavalrymen were taken by surprise and many of them retreated in panic. The Confederate cavalrymen dismounted and took up positions on both sides of the road. When the Federals returned, Emack's men waited patiently until they were about 10 yards away and opened fire. The Union cavalrymen were convinced they were opposed by a much larger force. While this standoff continued, Ewell's wagons were moving as swiftly as possible to get out of range of the Union cavalry threat.

By the time Grumble Jones was able to make his way to the scene through the crowded roads, the small Maryland detachment had been driven back several hundred yards, almost to the road junction being used by the wagon train. By this time less than one half of the train had made it safely through the Pass. Jones promised reinforcements from the 6th Virginia Cavalry
6th Virginia Cavalry
The 6th Virginia Volunteer Cavalry Regiment was a cavalry regiment raised in Virginia for service in the Confederate States Army during the American Civil War. It fought mostly with the Army of Northern Virginia....

 and Emack ordered his men to hold their ground and conserve their ammunition. Meanwhile, elements of Jones's cavalry attacked Huey's brigade in the rear of Kilpatrick's column.

Kilpatrick brought forward two guns of horse artillery from Lt. Alexander C. M. Pennington's Battery M, 2nd U.S. Artillery, supported by men of the 1st Ohio Cavalry. South of the hotel, a bridge on the road had not been destroyed by the Confederates and Col. Russell A. Alger
Russell A. Alger
Russell Alexander Alger was the 20th Governor and U.S. Senator from the state of Michigan and also U.S. Secretary of War during the Presidential administration of William McKinley...

 of the 5th Michigan Cavalry requested reinforcements to make a mounted charge across the bridge. Kilpatrick ordered Custer to make the attack with his full Michigan Brigade
Michigan Brigade
The Michigan Brigade, sometimes called the Wolverines, the Michigan Cavalry Brigade or Custer's Brigade, was a brigade of cavalry in the volunteer Union Army during the latter half of the American Civil War...

. The advance of the 5th and 6th Michigan Cavalry regiments was slowed by the darkness, difficult terrain, and dense undergrowth. The tiny group of Marylanders, supported by a few cavalrymen from the 4th North Carolina of Robertson's Brigade, had delayed the Union advance for nearly five hours.

At about 3 a.m. on July 5, as the Michigan Brigade continued to move slowly forward, Kilpatrick sent in the 1st West Virginia Cavalry
1st West Virginia Volunteer Cavalry Regiment
The 1st West Virginia Volunteer Cavalry Regiment was a cavalry regiment that served in the Union Army during the American Civil War.-Service:The 1st West Virginia Cavalry was organized at Wheeling, Clarksburg, and Morgantown in western Virginia between July 10 and November 25, 1861.An analysis of...

 under Major Charles E. Capehart. Capehart's 640 officers and men charged what they imagined to be "five times" their numbers. In hand-to-hand fighting with sabers and revolvers, they seized the Confederate cannon and Capehart was later awarded the Medal of Honor
Medal of Honor
The Medal of Honor is the highest military decoration awarded by the United States government. It is bestowed by the President, in the name of Congress, upon members of the United States Armed Forces who distinguish themselves through "conspicuous gallantry and intrepidity at the risk of his or her...

 for his gallant service. The road was open to attack the wagon train.

Attacking the wagon train

The Union cavalrymen crashed into the column of now lightly protected wagons. Custer, in his enthusiasm for the charge, was thrown from his horse and nearly captured. Grumble Jones also narrowly avoided capture. Pennington's artillery began shelling the wagons toward the rear of the column, splintering carriages and blocking any opportunity for retreat. The Union and Confederate cavalrymen became thoroughly mixed up among the wagons and the enemies were unable to differentiate themselves in the darkness. Several friendly fire
Friendly fire
Friendly fire is inadvertent firing towards one's own or otherwise friendly forces while attempting to engage enemy forces, particularly where this results in injury or death. A death resulting from a negligent discharge is not considered friendly fire...

 incidents occurred as Union troopers accidentally fired on their own lines.

Union troopers rode all the way through the wagon train until they reached Ewell's infantry and captured large numbers of prisoners before returning to repeat the effort. They erected hasty barricades in front of the wagon train to protect what they had captured. More than 1,300 Confederates—primarily wounded men in ambulances, but also slaves, free blacks, and some cavalrymen—were captured and most of the wagons were destroyed. Many of the mules survived and were turned over to the Cavalry Corps quartermaster
Quartermaster
Quartermaster refers to two different military occupations depending on if the assigned unit is land based or naval.In land armies, especially US units, it is a term referring to either an individual soldier or a unit who specializes in distributing supplies and provisions to troops. The senior...

. Kilpatrick later reported that he had destroyed Ewell's entire wagon train, although he had in fact encountered only a fraction of the full, 40-mile long train. The Confederates lost about 250 wagons and ambulances with casualties from Iverson's
Alfred Iverson, Jr.
Alfred Iverson, Jr. was a lawyer, an officer in the Mexican-American War, a U.S. Army cavalry officer, and a Confederate general in the American Civil War. He served in the 1862–63 campaigns of the Army of Northern Virginia as a regimental and later brigade commander...

 and Daniel's
Junius Daniel
Junius Daniel was a planter and career military officer, serving in the United States Army, then in the Confederate States Army during the American Civil War, as a brigadier general. His troops were instrumental in the Confederates' success at the first day of the Battle of Gettysburg...

 Brigades and of three artillery battalions, as well as 37 wagons from Maj. Gen. Robert E. Rodes
Robert E. Rodes
Robert Emmett Rodes was a railroad civil engineer and a promising young Confederate general in the American Civil War, killed in battle in the Shenandoah Valley.-Education, antebellum career:...

's division quartermaster trains.

Aftermath

Following the fight at Monterey, Kilpatrick's division reached Smithsburg
Smithsburg, Maryland
Smithsburg is a town in Washington County, Maryland, United States. Its population was 2,146 at the 2000 census and latest 2008 estimates are at 2,908. Smithsburg is close to Fort Ritchie army base and just west of the presidential retreat Camp David....

 around 2 p.m. on July 5. Stuart arrived from over South Mountain with the brigades of Chambliss and Ferguson. A horse artillery
Horse artillery
Horse artillery was a type of light, fast-moving and fast-firing artillery which provided highly mobile fire support to European and American armies from the 17th to the early 20th century...

 duel ensued, causing some damage to the small town. Kilpatrick withdrew at dark "to save my prisoners, animals, and wagons" and arrived at Boonsboro
Boonsboro, Maryland
Boonsboro is a town in Washington County, Maryland, United States, located at the foot of South Mountain. It nearly borders Frederick County and is proximate to the Antietam National Battlefield...

 (spelled Boonsborough at that time) before midnight.

Lee's retreat continued to the Potomac, as minor combat operations—primarily cavalry actions—occurred at Hagerstown
Hagerstown, Maryland
Hagerstown is a city in northwestern Maryland, United States. It is the county seat of Washington County, and, by many definitions, the largest city in a region known as Western Maryland. The population of Hagerstown city proper at the 2010 census was 39,662, and the population of the...

 (July 6 and 12), Boonsboro
Battle of Boonsboro
The Battle of Boonsboro took place on July 8, 1863, in Washington County, Maryland, as part of the Retreat from Gettysburg during the Gettysburg Campaign of the American Civil War....

 (July 8), Funkstown
Battle of Funkstown
The Second Battle of Funkstown took place near Funkstown, Maryland, on July 10, 1863, during the Gettysburg Campaign of the American Civil War...

 (July 7 and 10), and around Williamsport
Battle of Williamsport
The Battle of Williamsport, also known as the Battle of Hagerstown or Falling Waters, took place from July 6 to July 16, 1863, in Washington County, Maryland, as part of the Gettysburg Campaign of the American Civil War....

 and Falling Waters
Falling Waters, West Virginia
Falling Waters is an unincorporated census-designated place on the Potomac River in Berkeley County, West Virginia. It is located along Williamsport Pike north of Martinsburg. According to the 2010 census, Falling Waters has a population of 876....

 (July 6–14). At the Potomac, the Confederates found that rising waters and destroyed pontoon bridges prevented their immediate crossing. Erecting substantial defensive works, they awaited the arrival of the Union army, which had been pursuing over longer roads more to the south of Lee's route. Before Meade could perform adequate reconnaissance and attack the Confederate fortifications, Lee's army escaped across fords and a hastily rebuilt bridge.

Further reading

  • Laino, Philip, Gettysburg Campaign Atlas. 2nd ed. Dayton, OH: Gatehouse Press 2009. ISBN 978-1-934900-45-1.
  • Wert, Jeffry D.
    Jeffry D. Wert
    Jeffry D. Wert is an American historian and author specializing in the American Civil War. He has written several books on the subject, which have been published in multiple languages and countries.-Bibliography:...

    Custer: The Controversial Life of George Armstrong Custer. New York: Simon & Schuster, 1997. ISBN 978-0-6848-3275-3.

External links

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