This residential enclave was platted on a twentyacre tract that was, according to an early National Road milepost nearby, five miles from downtown Wheeling. Oliver Pryor, who bought the property in 1852, erected a brick house on it in 1853. When the tract was subdivided into eighteen lots in 1899, his former house was at the center of one of them. All lots fronted a single street, entered directly from National Road. Ten years later, almost all the lots had been built upon, and Highland Park was regarded as one of the city's best addresses.
The original entrance, with its massive stone gateposts, was designed by architect Frederic F. Faris. Unfortunately, it was demolished along with two of the earliest and most important houses when Interstate 70 was under construction in 1965–1975. Because of the interstate, Highland Park is no longer entered directly from National Road but must be approached from Lincoln Drive, which intersects with National Road southeast of the original approach. Even with these changes, the cul-de-sac keeps a distinctive private character. For the most part, its dozen or so houses display the easy informality typical of early suburban architecture. As if released from the restraints of narrow city lots, most of the houses have long, broad