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Timeline of Engagements
Order of Battle
The Battle of Monterey Pass
The Emmitsburg & Waynesboro Pike
The Skirmish of Fountain Dale
The Battle for Fairfield Pass
The Citizens Fight of Monterey Pass
The Retreat through Monterey Pass
Lt. Colonel Walter H. Taylor

Monterey Pass is located in the southeastern portion of Franklin, County Pennsylvania on South Mountain and is made up of two geographical mountain peaks. Mount Dunlap is 1,760 feet above sea level and Monterey Peak is 1,420 above sea level. The Monterey Pass area extends into four counties and is divided by two states along the Mason and Dixon Line. Franklin and Adams Counties make up the Pennsylvania side while Frederick and Washington Counties make up the Maryland side. Situated in the middle of Monterey Pass is the community of Blue Ridge Summit.

Situated on the Maryland Line at PenMar, the scenery of western portion of Monterey Pass has a breath taking view of the Cumberland Valley. Seen in the background is Waynesboro, Ringgold, and Greencastle. On the eastern side of Monterey Pass is Pine Mountain, Jacks Mountain and Raven Rock or Beard’s Hill as it was once called located near Fountain Dale. You can see portions of Harbaugh Valley, Gettysburg as well as Emmitsburg. Although being a small community today, Fountain Dale received its name because of the thousands of springs that flow from the mountains near Monterey Pass and flows into Toms Creek. Many spring houses can still be seen today.

Monterey Pass was a very important transportation route. The Emmitsburg and Waynesboro Pike was a major road that traveled over South Mountain and it intersected with several roads that led into Smithsburg, Fairfield Pass, Waynesboro, Emmitsburg and Mentzer Gap. The Emmitsburg and Waynesboro Turnpike was completed on September 21, 1820 as part of the Waynesboro, Greencastle and Mercersburg Turnpike Company.

 

 

 

 

 

 

 

 

 

 

Map of Military Operations July 4th - 5th

On the evening of July 4th, 1863, one of the most confusing battles of the Civil War occurred during the retreat from Gettysburg known as the battle of Monterey Pass. General Robert E. Lee had given the order to retreat from Gettysburg. Around 9:00 p.m. near Fountain Dale, Pa. the Union cavalry under the command of General Kilpatrick came in contact with the Confederate 1st Maryland cavalry under Captain George Emack, who had a small detail guarding the approach to Monterey, re-enforced by one cannon.

Darkness set in during a blinding rainstorm. The Confederates wearing gum blankets, were mistaken as Union troops by Kilpatrick’s cavalry as they made their way from Fountain Dale. Knowing that their identity was withheld, the order came from Emack to fire the cannon. As the confusion subsided, the Confederates charged, pushing the Federals back until they reached the Federal artillery that was at Fountain Dale. 

General Kilpatrick gained the mountain summit of Monterey six hours later. During the battle, General Kilpatrick sent a small force to Fairfield Gap, where they were beaten back by Confederate Cavalry. At the Monterey House, a Union battery deployed and began shelling the enemy’s wagons. By 3:30 a.m. the Union Cavalry reached the road where Ewell’s wagon train was located, capturing and destroying 9 miles worth of wagons, taking 1,360 prisoners and a large number of horses and mules as they moved on to Rouzerville.


Want to learn more about the area? Then try the Emmitsburg Historical Society