In 1788, Negley purchased a 278-acre farm along the Allegheny River that he called “Fertile Bottom” and which extended over much of what is now Highland Park north of Bryant Street.

Jacob Negley was one of the most prominent citizens in the early nineteenth century of the East Liberty Valley, the ancient river bottom that lies north of Squirrel Hill in the eastern section of Pittsburgh and provides relief from the generally hilly topography of the city.

This started the process of subdivision of land in East Liberty and Highland Park that led to the development of those neighborhoods in the later nineteenth century.

In 1870, the City Councils passed the Penn Avenue Act, which provided a mechanism for the paving of local streets, and in 1872 horse-drawn streetcar service was extended out of Pittsburgh to East Liberty.

In addition, the city Water Commission purchased land and began construction in 1872 of a reservoir on the top of the hill at the head of Hiland Avenue that opened in 1879.

These homes are spaced further apart than the rowhouses of fully urban neighborhoods such as Bloomfield and Lawrenceville, but they are much closer together than is typical in a post-1940s automobile suburb.

Due in part to the aforementioned decline of East Liberty, the Highland Park neighborhood developed a very small business district of its own on Bryant Street, which presently includes a number of restaurants, a neighborhood grocer, a bakery, a coffee shop, an automobile repair facility, and several other small businesses that are interspersed among private residences on Bryant Street.

[3] Academy Award-winning actor, Gene Kelly, and acclaimed jazz singer, Billy Eckstine, were both born and raised here.