The tour itself is roughly 22 miles and takes about an hour and a half 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. Click for a printable tour word document.

At Fairfield, General Ewell's wagon train was roughly 17 miles long with the contents of "plunder" gathered during the Pennsylvania Campaign, as a result of Confederate foraging from the farms of Pennsylvania. Through the driving rain, General Ewell’s wagon train rumbled out of Fairfield, traveling toward Jack’s Mountain. 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 Leitersburg.

From Fairfield, take Iron Springs Road and travel 3 miles to Gum Springs Road. Turn right onto Gum Springs Road. Gum Springs Road cuts between Pine Mountain and Kepner Knob and travels along Toms Creek. This is the road the Confederate wagon train was traveling on as it approached Fairfield Pass about 2 miles away.

This is the site of Fairfield Pass where Colonel Stagg ran into resistance from the Confederate cavalry and artillery. The road in the center of the woods is Maria Furnace Road that is now in private hands today.

There is no pull off spot for Fairfield Pass. Fairfield Pass was the scene of the cavalry fight between Colonel Stagg's portion of the 1st Michigan Cavalry, who attempted to attack the Confederate wagon train coming from Fairfield. This was the second pronged attack that was ordered by General Kilpatrick as he was attacking Monterey Pass. The original road can be seen today, but is on private property. Once you cross into Franklin County proceed to the top of the hill where the road levels out and turns toward the left.

Gum Springs Road becomes Furnace Road once you've crossed into Franklin County. Stay on Furnace Road another two miles until you see an intersection by the railroad tracks. This is old Waynesboro Road. Charmian Lane is directly in front of you. Turn left and proceed 1 mile to the Fountain Dale Fire Department located on your right at the bottom of the mountain. Park at the Fountain Dale Fire Department.

Stop 3, Fountain Dale Fire Department: Two interpretive panels are located on the site.

This is the direction that Kilpatrick's Cavalry traveled coming from Emmitsburg. The Fountain Dale Fire Department houses to markers that tell the story of Kilpatrick's movements toward Monterey Pass as well as the skirmish of Fountain Dale that occurred on June 28th, 1863.

Located in the Fountain Dale Fire Department’s parking lot you will see the Fountain Dale skirmish marker and a Monterey Pass Battlefield marker. This is not the site of the June 28, 1863 skirmish, but it is the site of where General Kilpatrick ran into a few of Captain Emack’s pickets. They were quickly overran and retired up the mountain to Monterey. As you travel up the mountain on Old Waynesboro Road, General Kilpatrick describes the road conditions his cavalry experienced. On his right was Monterey Peak which was a rough, rugged portion of Monterey Pass. To the left was a steep ravine and to his front was a road so narrow that he couldn’t even deploy his artillery.

From the Fountain Dale Fire Department make a left and travel up the mountain in the direction you just came. As you re-cross the railroad tracks, this is where the battle of Monterey began. As you cross the railroad tracks, you'll notice a curve in the road in front of you to the left. This is where the Clermont House once stood behind the pine trees. Once the road straightens and begins to level out, this is where is the first portion of the battle of Monterey began.

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David Miller monument. He was the builder and owner of the Clermont House. He served as a Union scout during the battle of Monterey Pass.

Stop 4, The David Miller Monument:

Pull into the parking lot of the Hawley Memorial Church and walk toward the main road. Walking due east down the road you’ll see a monument for David Miller.

David Miller was the formal manager of the Monterey House. At the onset of the Civil War he was in the process of building the Clermont House. As he was taken prisoner, he was held at the Monterey House. His expertise helped to guide General Kilpatrick’s cavalry during the confusing fight at Monterey Pass. This is also the area where the Clermont House once stood. The monument stands near the hedge row on your right as you walk down the road a short distance from Hawley Memorial Church. As you walk down to see the monument look back up the hill from where you were to see where Captain Tanner deployed one cannon.

After viewing the monument walk back up the hill to Hawley Memorial Church.

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This is the site where Captain Tanner deployed his cannon. This picture was taken near the spot where the limber would have been deployed.

Stop 5, Hawley Memorial Church: Two interpretive panels is located on the site just on the other side of the bushes by the roadside parking.

Two interpretive panels are located on the site that explains the Confederate artillery position as well as the opening phase of the battle of Monterey Pass. It is at this location that Captain Tanner’s artillery piece fired into the 5th Michigan. The shots were fired too high to cause much harm, but it caused much confusion in the ranks of the 5th Michigan. Kilpatrick ordered the 8th Pennsylvania to dismount and attack Emack via the Clermont House. Captain Emack had pulled his men back to the Monterey House forcing Tanner to leave his limber behind where it was captured. Emack was then forced to withdraw from the Monterey House back toward Monterey Pass.

Once you read the interpreter panels, walk westward to the intersection of Monterey Lane.

Stop 6, The Corner of Monterey Lane:

The Monterey House after the Civil War.

The series of Pine trees to your left of the Monterey Lane is where the Monterey Inn once stood. General Kilpatrick stopped at the Monterey House where David Miller and Jacob Baer were being held prisoner. Mr. Miller and General Kilpatrick discussed the roads of the area and where they led. Mr. Miller informed General Kilpatrick of Mount Zion Road through Raven Rock that led into Smithsburg and Leitersburg. General Kilpatrick sent the 1st Vermont Cavalry down Monterey Lane taking Mr. Buhrman as their guide to Smithsburg. General Kilpatrick also ordered Colonel Town to take a regiment to head off the wagon train East of Monterey. A portion of the 1st Michigan Cavalry under Lt. Colonel Peter Stagg was sent upon modern day Furnace Road that led to Fairfield Gap in order to try to head off the Confederate wagon train traveling toward Monterey Pass one mile away. This area is where General Kilpatrick ordered Pennington’s Battery to deploy in order to support General Custer’s battle line that had stalled near the area of the Rolando Woods Lions Club Park. General Kilpatrick also sent the 1st West Virginia Cavalry to support General Custer.

From Hawley Memorial Church, continue on Old Waynesboro Road, passing the Monterey County Golf Course, for about a half of mile. You will see Rolando Woods Memorial Park, that will be on your right. Route 16 is directly in front of you. Park at Rolando Woods.

Stop 7, Rolando Woods Lion’s Club Park: One interpretive panel is located on the site as well as a Pennsylvania Civil War Trails Wayside Exhibit.

This is the area where some of the hardest fighting took place. The bridge you see here is where the artillery piece was positioned and then fell back over a wooden bridge that once stood here. The cannon then was positioned near the last white building you see in the photograph.

Rolando Woods Lions Club Park is where General Custer attacked Captain Emack at the pass and could see the wagon train toward his right as it came upon the Emmitsburg and Waynesboro Pike. The old tollhouse is located across modern day Route 16. This is where the old Furnace Road, Mentzer Gap Road and Pennersville Road intersected with the old Emmitsburg and Waynesboro Pike. This section is where General Custer’s men over ran Emack who was reinforced by the 6th Virginia and the 4th North Carolina Cavalry. Crossing Red Run Creek, Custer sent the 1st West Virginia Cavalry charging through and they started destroying wagons and taking on prisoners. Kilpatrick kept this up until he was at the base of the mountain in Waterloo, known as Rouzerville today. As you travel down the mountain, you’ll notice on your right, that the mountain starts to descend. This is the area that is often described as where the wagons were forced off of the cliffs trying to out run General Kilpatrick’s cavalry.

Use caution and cross over Route 16 (Buchanan Trail) and continue on Old Waynesboro Road to Rouzerville. Once you are nearing Rouzerville, you will see a yellow caution road sign for a 20 mile per hour sharp right-hand turn with a road directly in your front. This is Waterloo Road. Take Waterloo Road to PenMar Road. Notice Harbaugh Church Road is directly in front of you. Make a left on PenMar Road and travel up the mountain. Once you are at the top of the mountain, you’ll see a stop sign. Make a right onto High Rock Road and travel to PenMar Park. Park at PenMar Park.

From PenMar Park one can see the Cumberland Valley looking toward Waynesboro.

Stop 8, PenMar Washington County Maryland Park: A Maryland Civil War Trails Wayside is located at the park.

From Rolando Park to PenMar Park is about 4 miles. PenMar Park sets at an altitude of 1400 feet, and offers one of the finest scenic views in Maryland with a clear view of the Cumberland Valley. Bathrooms are located on the premises.

From PenMar Park continue up the mountain on High Rock Road for about 2 miles to High Rock. Parking is located on your right. Warning, use caution as this is not handicap accessible nor are there any guard rails. Please caution children when on High Rock. If you’re afraid of heights, then proceed to stop 10.

High Rock offers a view of Waynesboro, Ringgold and Smithsburg and one can easily see Kilpatrick's movements as he left Ringgold to Smithsburg.

Stop 9, High Rock Washington County Maryland Park:

Standing on the highest point of South Mountain in Maryland, High Rock offers a fine view of the Cumberland Valley. This area was used by Union troops serving in the Signal Corps in 1864 as they witnessed the burning of Chambersburg. At High Rock you can see Smithsburg to your extreme left and Ringgold in the center and Waynesboro to your right.

Retrace your route back to PenMar Park to PenMar Road. Make a left turn on PenMar Road continue down the mountain until you reach Harbaugh Church Road. Make a left on Harbaugh Church Road and continue to SR-418 (Midvale Road). Make a left onto Midvale Road. At the Maryland Border Midvale Road becomes State Route 418. Turn right on to Misty Meadow Road. You'll see a red brick building ahead near a cemetery to your left. This brick building is called the Ringgold Meeting House and was not here during the Civil War. The original school house sits along Windy Meadow Road which is on the left as your traveling toward the traffic light at Ringgold.

Stop 10, Ringgold, Maryland:

General Kilpatrick traveled to Ringgold, where he ordered his division to halt after the battle of Monterey Pass and the affair at Waterloo. The casualties of these battles proved to be devastating for the Confederates. General Kilpatrick stated his losses at Monterey Pass were 6 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 and along the Waynesboro and Emmitsburg Road.

Travel back to MD Route 418. Make a right onto 418 (Midvale Road) and follow it to the flashing four way stop, this is the Smithsburg Road. You can go to Hagerstown, Leitersburg or Waynesboro from this point. Go through the flashing lights staying on Route 418 for about 2 miles and a make a left onto Ringgold Street in Leitersburg.

Stop 11, Leitersburg, Maryland: Two Maryland Civil War Trails Wayside Exhibits located on Ringgold Street.

Raven Rock Pass is seen about six miles away from Leitersburg.

This is the scene where the 1st Vermont attacked several wagons. After coming off of the Leitersburg and Smithsburg Turnpike, the 1st Vermont Cavalry came upon a Confederate Wagon train that was coming from the direction of Monterey Pass and Waynesboro. Because of the rolling hills and darkness, the Confederate Wagoner's had no chance. Once the 1st Vermont began attacking and taking on prisoners, the 1st Vermont separated sending a small force to Hagerstown and Boonsboro. Another portion traveled back to Ringgold and met up with General Kilpatrick. 

Continue into Leitersburg and by the old Leitersburg Inn, turn left onto the Leitersburg and Smithsburg Pike and travel to Smithsburg about 4 miles away. At the first traffic light turn left and follow it toward Route 64. A small road will be on your right just before the main road. Turn right and travel a short distance and pull off on the Cul-de-sac.

Stop 12, Smithsburg, Maryland: Two Maryland Civil War Trails Wayside Exhibits located in the Smithsburg Community Park.

Raven Rock Pass is toward the center of the photograph and Monterey Pass is to the left of the photograph. The fields in between is where the battle of Smithsburg occurred.

Operating behind Confederate lines at Ringgold, Maryland, General Kilpatrick was in a dangerous situation. Following South Mountain due southward, he pressed on to Smithsburg. Fearing a possible attack from the direction of Emmitsburg, General Kilpatrick sent scouts into the areas of South Mountain protecting his cavalry near Raven Rock Hollow Road. Kilpatrick later in the day battled two brigades of General JEB Stuart's Cavalry. Fearing the worst, Kilpatrick breaks off the engagement and head to Turner's Gap in order to seek safety.

From here you can make a left onto 64 to Hagerstown or following 64 to 997 to Waynesboro about seven miles away. The tour ends here at his point.