The Battle of Monterey Pass

Touring the area

Our Civil War walking tour will show you the Civil War sites of Emmitsburg or Monterey Pass. I will share with you pictures from the time period closely representing what area looked like during the time of Civil War. The tours are approximately one hour long. Our fees are $10.00 per-person with kids 10 years of age and under free of charge. All fees go back into our efforts of historical preservation and research projects.

The walking tour is a reserve basis, so let me know what times suit your family needs. If you plan a trip to the Gettysburg area and would like to tour, please feel free to contacts us!

Touring the Battle of Monterey Site:

This tour will start at Fairfield, Pa. and travel on Iron Springs Road to Gum Springs Road and come out at the intersection by the rail road tracks near Charmian. This intersection is Old Waynesboro Road. You will travel to Fountaindale at the base of the mountain, and travel back up to Monterey and continue through Monterey Pass to Rouzerville. From Rouzerville, you'll travel up the mountain to PenMar. From PenMar travel back down the mountain and end your tour at Ringgold.

The tour itself is roughly 20 miles and takes about a hour to do. The tour covers some of the most rugged mountain roads in the Monterey area. Please use caution when traveling these roads. The best time of the year to tour the Monterey area is from April to mid October.

Touring the Emmitsburg & Waynesboro Turnpike:

The Emmitsburg and Waynesboro Pike was a major road that traveled over South Mountain and had several key intersections that connected to it. Zora was only a crossroad at the time of the Civil War. It was where the Emmitsburg-Waynesboro Road and the Fairfield Road came together, and both armies felt the need to obtain and protect their positions at these crossroads and mountain gaps to see the troop movements in the direction of Emmitsburg, Waynesboro or Fairfield.

Six miles north of the Mason and Dixon Line is a little town called Fountaindale. Fountaindale is located between Jack's Mountain, Beards Hill, on the Old Waynesboro Pike. Pegram's Artillery reached Maryland late in the evening on June 25th, crossing the Potomac River at Boteler's Ford. From there they traveled the roads that led into Hagerstown. After reaching Fayetteville, Pa., their horses were done in and they needed fresh horses. Lt. Chamberlayne took a 25 man detail into Adams County to Fairfield.

On June 28th, 1863, Fountaindale was the first skirmish in Adams County according to several veterans of Cole's Cavalry. It was here that a Confederate 25 man foraging party coming in from the direction of Fairfield came upon a small church. The foraging party took the horses but not before they were spotted by members of Cole's Cavalry Company C under Lt. William Horner.

Areas of Interest

Touring the Thurmont Area:

In October of 1862, Union Cavalry General Alfred Pleasonton used the Thurmont area to scout and pursue Confederate General Jeb Stuart's Cavalry during the Chambersburg Raid. The year during the Gettysburg Campaign of 1863, portions of the Army of the Potomac traveled through Thurmont. Union General Wesley Merrit's Cavalry Brigade was ordered to guard the roadways and communication lines and the mountain passes in the Catoctin Mountains near Thurmont.

After the battle at Gettysburg, General Merrit's troopers were ordered to guard Harman's Pass near modern day Camp David. This created a problem for General Stuart who at Thurmont learned of General Merrit's troops at Harman's Pass. General Stuart had needed at way get across the Catoctin Mountain and rejoin General Lee's retreating Army. Traveling toward Franklinville, General Stuart backtracked to Mount Saint Mary's College. Capturing several Signal Corps troops at Indian Lookout, near Emmitsburg Pass, General Stuart made his way through Eyler's Valley. During the pursuit of General Lee's Army, portions of the Union Army marched through Thurmont to Lewistown using the Catoctin Mountain at Hamburg Pass to cross into the Middletown Valley.

In 1864, after the battle of Monocacy, a force Confederate cavalry was in the Lewistown and Creagerstown area stealing horses. In the Sabillasville and Monterey area, 40 Confederate soldiers under General John Imboden's command were also spotted.

Discover Historic Civil War Emmitsburg:

William Emmit founded the town of Emmitsburg in 1785 and through the years Emmitsburg grew to become recognized as a symbol of religion due to its many churches such as Saint Joseph College, and Mount Saint Mary’s Seminary School. During the outbreak of the Civil War, many town residents mustered into the military fighting on both sides. As the Civil War progressed, Emmitsburg had split loyalties for the Union. Some men served as far south as the Carolinas, while others volunteered in the Maryland and Virginia Regiments in the Army of Northern Virginia.

The Emmitsburg area played a major role in the Civil War, more than what has been given credit and was a pivotal crossroad of the Waynesboro Pike. Emmitsburg witnessed every raid that carried over into Pennsylvania from JEB Stuarts’ first Chambersburg Raid of 1862, the Gettysburg Campaign in the summer of 1863 and finally, General Early’s Raids of July of 1864.