The Engagement of Iron Springs

On the morning of July 6, 1863, the Confederate army, having retreated from Gettysburg, took up their line of march on the Hagerstown Road. This road led directly to Fairfield, where it would transverse through Fairfield Gap and Monterey Pass on South Mountain. From Monterey Pass, the Confederate army would move into Waynesboro, Pennsylvania. Taking the Leitersburg and Antietam Road, the Confederate army would move directly into Hagerstown and Williamsport, Maryland. 

Encamped on South Mountain since July 5, Lieutenant General James Longstreet’s Corps marched up Jacks Mountain Road to the Emmitsburg and Waynesboro Turnpike and took the lead during the retreat. Following behind them, was Lieutenant General A. P. Hill’s Corps. The night prior, Hill’s Corps had taken the Hagerstown Road from Fairfield to Monterey Pass, where the corps encamped. Located behind them, was Lieutenant General Richard Ewell’s Corps. They had encamped near South Mountain the night before. 

Early in the morning of July 6, the Confederate army began its movement to Waynesboro. Lieutenant General  Ewell had ordered Major General Robert Rodes to take his division and relieve Major General Jubal Early’s Division, who had skirmished with portions of the Union VI Corps at Fairfield. Major General Early was ordered to lead Ewell’s Corps for the duration of the day. 

While the Confederate army issued marching orders to march toward Waynesboro, Major General John Sedgwick and his VI Corps made plans to harass the rearguard of the Confederate army. Major General Sedgwick ordered Brigadier General Thomas Neill and his brigade of infantry to lead the attack. Brigadier General Neill’s brigade consisted of six companies of the 7th Maine Infantry, a detachment of the 33rd New York Infantry, 43rd New York Infantry, 77th New York Infantry, and the 61st Pennsylvania Infantry. 

The Reed Farm looking toward the Union position

Major General Rodes deployed his division with the brigades of Brigadier General George Doles to the right of the Hagerstown Road and Brigadier General Junins Daniel’s brigade on the left of the road, near the Reed farm as skirmishers. With Iverson’s brigade already ahead of the main army, Ramseur’s Brigade and O’Neal’s Brigade would not participate in the action.1

Close to the battle line

Brigadier General Neill deployed his brigade in skirmish formation and proceeded to move toward the Confederate line. Their line stretched out one to two miles long when the attack was launched.  With Brig. Gen. Daniel’s brigade occupying the Reed farm, some of the Union troops had entered the orchard behind the farm house and hit the 45th North Carolina with Captain J. A. Hopkins commanding. This regiment was on the extreme left, located in front of the Reed farm. Upon reaching the hill, Captain Hopkins was ordered to surrender. Captain Hopkins charged the enemy’s position and forced them from the hill. Casualties totaled nine men lost, 2 killed, 2 wounded, and 5 missing. Captain Hopkins and the rest of Daniel’s brigade occupied the hill leading into the entrance between jacks Mountain and South Mountain. A portion of Brig. Gen. Doles’s left flank repelled an attack with no casualties.2  

The engagement of Iron Springs was over as soon as it began. With a strong Confederate rearguard in their front, it was determined that they should now begin to fortify South Mountain at the entrance of Fairfield Gap. The Union troops pulled back to Fairfield and halted. The Hagerstown Road was now clear for about five miles behind the Confederate army. The last of the Confederate skirmishers began marching through Monterey Pass with no further annoyance by the Union troops. 

The VI Corps was ordered to Emmitsburg, Maryland, and Brigadier General Neill was detached to operate as a light division. Colonel John McIntosh’s brigade of cavalry was assigned to Neill’s command as well as two pieces of artillery from Lieutenant Martin’s battery. They were ordered to harass the Confederate rearguard, but not to fully engage them. By evening, the Confederate army was concentrated in and around Waynesboro and Leitersburg, Maryland. Neill’s brigade would encamp near Monterey Pass.3 


  1. Report of Maj. Gen. R. E. Rodes, O.R.– SERIES I–VOLUME XXVII/2 [S# 44]
  2. Ibid, Report of Brig. Gen. Junins Daniel, O.R.– SERIES I–VOLUME XXVII/2 [S# 44]
  3. O.R.–SERIES I–VOLUME XXVII/1 [S# 43] — Gettysburg Campaign

Roads of Monterey Pass

Recently, on Penn Pilot, a website of aerial photographs of Pennsylvania, I am able to help explain visually what Monterey Pass looked like at least during the 1930’s as Route 16 or Sunshine Trail was being cut in. The roads that were used during the Civil War are still visible and still in use as this new highway was being cut in.

This map is a early 1900’s map of Monterey Pass. The map shows the layout of all of the roads in the area. 
Here is a 1937 aerial view of the Monterey Pass. You can still see all of the roads and the construction of Route 16. See the next photograph for the labeled roads.
This is a fairly good aerial view of Monterey Pass. You can still see all of the network of roads. The toll house is located on Waynesboro Road where Pennersville Road connects between the triangle.  
Here is a 1957 aerial view of Monterey Pass after Route 16 has been completed. 
A modern day view of Monterey Pass. Notice how many of the roads are no longer visible from the air. Where you see the word Monterey, this is where the golf course is located. 

Operations of South Mountain During Early’s 1864 Raids

South Mountain witnessed much activity during the American Civil War, most famously the Battles of South Mountain in September 1862. During the 1863 Pennsylvania Campaign the majority of SouthMountain in Maryland and Pennsylvania, saw much activity including the Battle of Monterey Pass, situated along the Mason Dixon Line. In July of 1864, South Mountain would again see major activity during Confederate Lieutenant General Jubal Early’s Maryland Campaign.

On July 3, many citizens living in the Cumberland Valley heard cannon fire in the direction of West Virginia, and began to flee, crossing South Mountain in the wake of another Maryland Invasion. It was rumored by many refugees that Lt. Gen. Early was leading an army toward Shepherdstown, and would ford the Potomac River there into Maryland. As many refugees flocked east of South Mountain, Middletown residents doubted that another invasion was even going to take place.

Headquartered in Baltimore, Union Major General Lew Wallace heard the same rumors about a massive troop movement moving up the Shenandoah Valley, that could threaten Maryland or Washington. He had also received reports about Lt. Gen. Early’s movements from the officials of the Baltimore and Ohio Railroad. Major General Wallace thought to himself about the consequences of this campaign. If Washington was the Confederate target, they could capture the defenseless city, as most of those troops were sent to Union General U. S. Grant.  If the city was lost, the Confederates would capture the Quartermaster Depot, Naval Yard, and the U.S. Treasury. This would be a major blow to the Union.

The Confederate army began to ford the Potomac River on July 5. By July 7, they were fully concentrated at Sharpsburg, where in September 1862, many of these men fought in the battle of Antietam. Major General Wallace boarded a train at Baltimore and made his way to Frederick. From there he began assessing his situation and weighing his options. Union cavalry stationed in Frederick also went out to assess the situation. There, at Turner’s Gap, upon SouthMountain, a detachment of the 8th Illinois Cavalry skirmished with Brigadier General Bradley Johnson’s Cavalry Brigade. This was no contest for the Confederate cavalry, and they pushed ahead toward Middletown when two cannon were fired by Alexander’s Baltimore Artillery, supported by the 8th Illinois Cavalry. Brigadier General Johnson and his cavalry would skirmish toward Braddock’s Gap upon the CatoctinMountain.

During the day, Lt. Gen. Early ordered his army to SouthMountain, skirmishing at several points along the way with Union Major General Franz Sigel’s force. Confederate Major General John C. Breckenridge marched into Rohrersville, where he was supplied with new shoes for his soldiers, and encamped for the night. A few miles to the south, Major General Robert Rodes’ Division skirmished with Union cavalry, but by nightfalll the Confederates were bivouacked near Crampton’s Gap. Lieutenant General Jubal Early, along with Major General Stephen Raseur’s Division were near Boonsboro.

Acting on orders, Mr. Flechter scouted the movements of the Confederate army. Reporting back to Major Burt about the activity near Boonsboro, Mr. Flecther recalled, “Discovered a large number scattered all over the country, gathering horses, with scouts in mountain for the same purpose, preventing my going any farther, and have gathered in a large number of horses from the Maryland farmers.” Major Burt sent that information to Major General Darius Couch in Waynesboro, Pennsylvania.

On July 8, Early’s army began marching toward Middletown. The Confederate army marched over SouthMountain at three different mountain gaps. Using the National Road through Turner’s Gap was Lt. Gen. Early and Maj. Gen. Ramseur’s Division. Also, the wagon train that followed the Confederate army used that same route. About a mile to the south was Fox’s Gap, situated on the Old Sharpsburg Road. Following this route was the Army of South Western Virginia under the command of Major General John C. Breckenridge. About seven miles south of that point was Crampton’s Gap. This is the route Major General Rodes’ Division would use.

Since the Old Sharpsburg Road and the National Road both led to Middletown, this would be the concentration point by evening for both Early and Breckenridge. Major General Rodes would continue his march to the town of Jefferson. The only natural barrier that separated the Confederate army from Frederick was the Catoctin Mountain.

As the Confederate troops moved over SouthMountain, the Union cavalry skirmished with the Confederate rear guard. By the end of the day, Crampton’s Gap was being used to hold Confederate prisoners that were captured by the Union cavalry.

As the sun rose on July 9, the Battle of Monocacy would erupt. While, Lt. Gen. Early was there fighting, he maintained a chain of pickets that covered many of the mountain gaps situated upon SouthMountain. Federal scouts entered Wolfsville, where they stated that fifty Confederate infantrymen were on picket duty, and that they were part of a chain of pickets that stretched across South Mountain from there to Boonsboro. It was also reported that several Confederate troops were fortifying the battlefield of South Mountain.

On July 10, it was reported that Confederate cavalry were foraging SouthMountain from MontereyPass to Frederick, stealing horses, and creating much alarm. During the day, Major John Burt wrote to Major General Couch, who was at Chambersburg, that about 3,000 cavalrymen under General Bradley Johnson were in Lewistown and Creagerstown, with another 7,000 cavalrymen at Smoketown. He also confirmed that the Confederate troops were fortifying South Mountain, and that General Imboden, with about 1,500 men, came down the west side of South Mountain, sending a small detail of men into Smithsburg, eight miles from Waynesboro, Pennsylvania.

Captain Maxwell Woodhull, who was serving as Acting Assistant Adjutant-General wrote a dispatch to Union Lieutenant Colonel Lawrence that Brigadier General William Morris wanted a cavalry to scout the area near SouthMountain at BlackRockBridge. Reports were of Confederate cavalry and a section of artillery moving along the Westminster and Baltimore Pike, from Boonsboro. The Westminster and Baltimore Pike was a roadway that led from Hagerstown, over SouthMountain at Wolf’s Tavern, and at the CatoctinMountain to Emmitsburg, and continued to Westminster.

This ended the actions on South Mountain during Lieutenant General Jubal Early’s Raid on Washington.  This campaign is a fascinating one. Although, the majority of the Confederate army marches toward Frederick and fights a battle along the banks of the Monocacy, one can see how far the effects of the campaign reached. Troop movements, picket lines, and smaller raid parties had a far reaching effect on the communities on and around South Mountain.