The Cobblestone Path is significant under criterion A as a remarkable example of late 18th century paved roadway which was probably the most important single-entry point to the street plan of Bardstown, Kentucky between 1785 and 1825. The steep incline was the final approach, the last few hundred feet of various roads and traces including the Wilderness Road. They had combined by intersections further east, then entered Bardstown by this single artery, thus connecting it with the great settlement area of the central Bluegrass region and the old settlements east of the Mountains. Improved by order of Congress and the Kentucky legislature before 1800, this avenue for pedestrian, wheeled and mounted traffic played a vital role in commerce and transportation during the earliest decades of development for Bardstown and central Kentucky. The rare survival of this stone paved road illustrates the permissible grades resulting from adapting to natural features during the earliest period of Kentucky's public improvements.

Connecting to the east end of Flaget Avenue in Bardstown, Kentucky, the cobble paved roadway ascends the eastern bluff overlooking the Towne Branch of Stewart's Creek on a sharp tangent from northeast to southwest. At the bottom, the hand-laid paving ends abruptly where the old roadway was cut off by ditching for east Broadway (also called Powerhouse Hill). Near the top, as the cobbled way curves toward a junction with present day Flaget Avenue, the paving disappears under earth fill which was applied during street modernizing sometime after 1900.

Near the top of the cobbled path as the curve begins toward 1st and Flaget Streets, the cobbled surface is embraced by natural limestone outcroppings on both sides. On the downhill or east side, this formation is raised twenty to thirty inches above the cobbles and resembles a very large irregular table top and close-by the road surface serves as a ready bench. By using it as an access walkway and pursuing the same formation south and east, this jutting, flat topped rock becomes the local look-out point called Lovers Leap which was a favorite outing and picnic spot in the period after the Civil through the end of the 19th century.

Below the Leap-Lookout perhaps 25 or 30 feet and physically somewhat south, is a small, dry cave which also was made famous by romantic stories of the 19th century. The mouth of the cave is located about equidistant from top to bottom on the face of the cliff and is physically difficult to reach either from above or below. - David H Hall, Preservation Program, City of Bardstown