Greensboro, a small and serene town nestled in a bend of the Choptank River, is about six miles north of Denton. Here are a number of good Federal and Victorian structures and inescapable flavor of nineteenth century, with its less hurried pace.

In 1732, the Maryland Assembly passed an act which was intended to found a town at the bridge near the head of the Choptank River, a point where the meandering stream described an s-shaped curve known as the "Great Bend"

A plat of this proposed town, to be known as Bridge Town, can be found in the land records of Dorchester County. The original owner was an enterprising native of Dorchester County named Peter Rich. A merchant, innkeeper and considerable landowner, Rich crossed the Choptank in 1732 and patented the thirty-one acres of lowland in the Great Bend of the river adjoining the western end of the bridge, which tract he named, not coincidentally, "Bridge Town".

Most local authorities have designated 1732 as the year when the town of Greensboro was founded. It has been proven by Eleanor Horsey, however, that this early plan for the founding of Bridge Town was notably unsuccessful; the area was still too sparsely populated and through traffic not yet sufficient to support a town.

In spite of the setback, Peter Rich prospered in the area. In 1736 he purchased a 200-acre tract called "Ingrams Desire" that adjoined the "Bridge Town" tract and included the major portion of the hill above the western end of the bridge. He also amassed more than 1000 acres on the other side of the river.

By 1747, Rich had deeded half of "Ingrams Desire" to his daughter Sidney and her husband Nathan Harrington. Their son, Peter Harrington, in turn acquired this property in 1778, along with other lands. The following year he began to sell lots in what was to become the town of Greensboro.

The new town, known as Choptank Bridge, took root on a hill to the west of the ill-fated Bridge Town. Harrington initiated the development of his property at the point where the road that ran from the Choptank River crossing southwest to Tuckahoe Bridge was joined by the road that ran south from Nine Bridges (modern day Bridgetown). These were the main traffic and trade routes through the area and nine lots fronting these roads were sold between 1779 and 1785. The original layout of Greensboro was not, therefore, the product of a conscious and pre-arranged design, so much as it was a response to the advantage and the shifting nature of a rural crossroads.