The area was not regularly occupied until it became the nation's capital on July 16th, 1790. The land was still predominately agrarian and was organized around the large land grants from the English crown. These settlements were 1,000 acres and larger.
The most important crop was tobacco, which was shipped to European markets for sale. Shepherd Parkway originally was part of the Gisbrough (later Giesborough and now Giesboro) land tract patented by Thomas Dent.
In 1833 the land was purchased by George Washington Young. Mr. Young managed many farms and was most notable as the largest slave holder in the District of Columbia. According to the 1850 US census G.W. Young owned 91 slaves. Among Mr. Young's land holdings was the 624 acre Giesborough (now Giesboro) plot as well as many other surrounding land tracts. The Young family grew a variety of crops, maintained livestock, harvested trees (mostly on the unimproved Saint Elizabeth plot for construction of the Federal Hospital for the insane in 1852) and due to the Young's land holdings along the confluence of the Potomac and Eastern Branch River (now Anacostia River) the family was able to ship their goods to market from their family wharf at Giesborough point.