Clearing the Mountain Range, Notes on the Road System

Every year, I always receive questions about the roads that led over South Mountian and why they were important. To answer these questions, I had to hit up the Maryland State Archives online to find answers to these questions. I also receive questions about the starting point and ending point of South Mountain and what classifies a mountain gap or mountain pass. Now the roads listed in this blog posting is not complete by any means. These are considered to be the main traffic routes from the 1700’s to about the time of the American Civil War.

South Mountain is a mountain range that covers three states. Near Hillsboro, Virginia, South Mountain is known as Short Hill Mountain and covers an area between Hillsboro and Leesburg that follows the Potomac River. South Mountain then extends into Maryland at Knoxville and crosses into Pennsylvania at Blue Ridge Summit and ends at Dillsburg as a series of small hills near the Susquehanna River outside of Harrisburg, covering a distance of more than seventy miles.

South Mountain consists of several mountain gaps and passes. Typically the definition of a mountain pass is a location in a range of mountains that is lower than the surrounding peaks. A mountain gap travels between mountain peaks. During the Civil War the armies waging campaigns into Maryland and Pennsylvania used many of the gaps and passes on South Mountain.

There are many gaps in Maryland that were used during the Civil War. During the Battle of South Mountain, there were five main gaps on South Mountain that were used by the opposing forces. Brownsville Pass is located near Brownsville and that road today is no longer used. One mile to the north is Crampton’s Gap which is located where the Arnoldstown and Gapland Roads intersect. Fox’s Gap is located on the old Sharpsburg Road known today as Reno Monument Road. Turner’s Gap is located on the old National Road between Middletown and Boonsboro. Above Turner’s Gap you have two roads that connect to Frostown, which the gap is named after. In the middle of South Mountian in Maryland you have Olier’s Gap which would be considered to be mondern day Route 40 or the Baltimore Road as it was called. Toward the northern section of Maryland, Wolf’s Tavern Pass connects the Thurmont area to the Smithsburg and Cavetown area. Raven Rock Pass is located on a section of roadway that once traveled from Hagerstown to Westminster.

Crossing into Pennsylvania, you had three main mountain passes that were used extensively during the Pennsylvania Campaign. Monterey Pass connects Emmitsburg and Waynesboro with the Fairfield Road that leads through Fairfield Pass. Traveling from Chambersburg to Gettysburg one must pass through the Cashtown Gap.

As discussed in the previous two paragraphs, the mountain gaps or mountain passes are located on a series of roads. Many of these roads were established in the mid 1700’s for the purpose of increasing settlements west of South Mountain. For example on April 30, 1751, a road from Williby’s Gap was built and connected to the road that led to Yorktown. This was first known as Nichol’s Gap and was part of the Great Wagon Road from Philadelphia. Williby’s Gap became known as Monterey Gap.

In 1774, the Maryland General Assembly wanted to improve the quality of the land, and to promote an increase in settlements, as well as cultivation of the land. In doing so, Maryland wanted to expand and improve their roadway system to promote exported goods, and to make it easier, and cheaper to increase trade from Frederick County to Baltimore County. The Maryland General Assembly appropriated eight thousand dollars to Frederick County for the use of laying out and expanding the roadway. This was to be done by opening, straightening, widening, repairing, and putting it in good order. South Mountain was part of this agreement, as it would have a roadway from the Conococheague Creek, crossing over Turner’s Gap to Frederick, while another road leading from Hagerstown would intersect the western base of South Mountain leading to Turner’s Gap.

On September 6th, 1776, it was announced that two new counties would be formed. On October 1st, 1776 Washington County and Montgomery County were formed when two portions of Frederick County were separated. The ridge of South Mountain was used as a boundary from the Potomac River to Pennsylvania where the line separating Frederick County and Washington County was temporarily drawn. Anything west of South Mountain was now known as Washington County.

While surveying the best route for the road a serviceable wagon path was discovered. The wagon path connected to Charlton’s Gap on South Mountain, and had the advantage of completing what was required by the General Assembly. If the wagon road could be used, it could be extended to facilitate the transportation of produce that could extend from Cumberland County in Pennsylvania to the Allegheny Mountains and travel to Baltimore. The subjects of Maryland would be better enabled to pay their taxes, and would increase the trade in Maryland.

On November 7th, 1779 a petition from John Summers and John Aulabaugh, of Washington County asking commissioners to alter and amend the roads from Turner’s Gap to Williamsport was taken into consideration. Another petition from Conrad Snavely, of Washington County, stated that the commissioners, under the act of assembly for straightening and widening the roads in Washington County, from Swearingen’s Ferry to the top of the South Mountain at Fox’s Gap, have laid a very considerable distance of road through his plantation, to his great injury, and that the road may continue in its old course, was preferred for consideration.

In 1782, the newly appointed commissioners of Washington County were authorized to lie out a main road at forty feet wide from Elizabethtown, through Washington County to hook up with Charlton’s Gap in South Mountain, where it would connect to Baltimore. On the eastern side of South Mountain in Frederick County, the commissioners of Frederick County were to construct a road that would connect to Charlton’s Gap, run through Frederick County, and intersect with the road leading from Frederick(town) to York(town) in Pennsylvania. The road was to be the nearest and best way to Baltimore as straight as the ground would permit with minimal damage to private property.

In 1791, more roadways in Frederick County were to be laid out, surveyed, marked and bounded. This applied to many of the roadways along the Frederick and Washington County line on South Mountain. From Middletown to Turner’s Gap, connecting to Fox’s Gap; from Charlton’s Gap to Libertytown,; from Baltimore County to Emmitsburg, Maryland to the Pennsylvania Line at Nicholson’s (Monterey) Gap. In Washington County the road leading from Fox’s Gap, through the town of Sharpsburg, and then to Swearingen’s Ferry was also to be marked and surveyed. All public roadways were to be supervised by a commissioner appointed by the Maryland General Assembly to oversee that all roadways were cleared at the same time.

In December of 1800, the petitions were heard in court. The court’s decision was in favor of the existing roads, one of which was the road leading from Fox’s Gap to Sharpsburg. The road from Fox’s Gap to Sharpsburg was deemed as a public road, and it was expected to be kept up as such. Any property damages were paid out to land owners, but not to exceed the rate of ten pounds per acre in current money.

On January 4th, 1812 it was approved to lay out, open, and cut a road not exceeding thirty-feet in width at the expense of Frederick County. The road would follow from Charlton’s Gap Road in Washington County, to the crest of the mountain in Frederick County to the divisional line. The road should not extend through any house, orchard, garden, or meadow unless with the consent of the owner or owners.

In 1816, an act of incorporation was passed in the Pennsylvania Legislature forming the Waynesboro, Greencastle and Mercersburg Turnpike Company. On September 21, 1820, the road was reported completed over the mountain from the Maryland line near Emmitsburg to the west end of Waynesboro. This roadway was part of the much bigger Baltimore and Pittsburgh Turnpike, but locally known as the Emmitsburg and Waynesboro Turnpike.

Leading from Hagerstown, crossing South Mountain near Wolf’s Tavern, and continuing to Thurmont was the Westminster and Hagerstown Turnpike that was completed in 1816. Near Wolf’s Tavern was another turnpike laid between South Mountain and the Catoctin Mountain that connected Emmitsburg to Frederick.

By the 1820’s, The first macadam surface in the United States was laid on the Boonsboro Turnpike between Hagerstown and Boonsboro, Maryland. Construction specifications for the turnpike road incorporated those set forth by John Loudon McAdam of Scotland. After side ditches were dug, large rocks were picked and raked. They were then were broken, not to exceed 6 ounces in weight or to pass a two-inch ring. Compacting work for each of the three layers was quickened using a cast-iron roller, instead of allowing for compacting under traffic.

It was these very roads during the American Civil War that would be used by both the Union and Confederate armies. These roads are described by many troops that marched upon them. Macadam roads tore up the soldier’s feet as they marched upon the hard, rocky surface, while dirt roads in foul weather made the march miserable. Remember that the infantry marched on these roads after the heavy wagons, cannon with their limbers, and caissons went through. Since the heavy wagons and cannon moved through first, often times they would unintentionally tear up the roads due to their weight, leaving it in an most undesirable condition for the soldiers to march upon. Many a soldier wrote about the road conditions during the retreat from Gettysburg, noting that the roads that led through South Mountain were the worst that they had seen for the duration of the war.


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