The neighborhood takes its name from Perrysville Avenue, which was itself named for
Commodore Oliver Hazard Perry, who supposedly used a Native American trail to transport supplies during the
War of 1812. Perrysville Avenue is an extension of Federal Street, the main north-south thoroughfare of the city formerly known as
Allegheny. It was previously a toll road known as the Perrysville Plank Road. Federal Street ends and Perrysville Avenue begins where the flat river plain gives way to a steep hill. A 1977 report about Pleasant Valley states that "Pleasant Valley was formerly known as Snyder's Hollow and its stream was a favorite ice skating spot. Primarily, the neighborhood was settled by Germans, Irish, Italians and Poles.
Josh Gibson, Hall of Fame catcher for the
Homestead Grays, a Negro National League team of the 1920s, lived there." The Charles Street Valley features rowhouses built by the owners of the Federal Street & Pleasant Valley Railway Co., which operated the streetcars that facilitated residential development in Perry South. A series of these rowhouses on Brightridge Street have been listed on the
National Register of Historic Places. Perry South experienced
white flight after 1960; from 1960 to 1970, the neighborhood's total population declined from 16,000 people to 13,000, while its
African-American population, which had formerly been located almost exclusively in the Charles Street Valley, increased from 15% to 20%. From 1970 to 2000, the total population decreased to just 5,200 people, of whom 65% were
African-American. For more than six decades, the Perry Hilltop Citizens Council has sought to improve housing conditions, advocate for residents, and to improve the neighborhood's business district. ==Surrounding Pittsburgh neighborhoods==