The tour itself is roughly 20 miles and takes about an 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.

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 Smithsburg.

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.

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. Please use caution as the Old Waynesboro Road is used as a main tractor trailer route and also be sure to watch speeding traffic.

Located in the Fountain Dale Fire Department’s parking lot you will see the Fountain Dale skirmish 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 drive: As you cross the rail road 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, this is where is the first portion of the battle of Monterey began. 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.

Pull over at the Hawley Memorial Church and walk a short distance toward Monterey Lane by the Golf Course. Look to your left. You'll see a single story yellow house. This is the area where the Monterey House once stood. This is also close to where General Kilpatrick was able to deploy his artillery to support General Custer who was attacking the Captain Eamck’s men at Monterey Pass. Monterey Lane by the Monterey Golf Course was used by the 1st Vermont Cavalry. They traveled to Smithsburg in order to cut off the head of the wagon train. This was Kilpatrick’s third prong attack that would be fought at the western base of South Mountain.

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

Rolando 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.

Stop No. 6, PenMar 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.

Retrace your route back to PenMar Road. Make a left hand 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.

Stop No. 7, 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 1 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.

The tour ends here. Travel back to MD Route 418. You can make a left and follow it to a stop light which is PA Route 16 or if you make a right from 418 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.