In 1788, Alexander Negley became one of the earliest settlers of the East Liberty Valley, moving his family west from Philadelphia to a 300-acre farm. Much of the land that today makes up Highland Park was part of Negley’s homestead, but it did not all become a park at once. Negley’s son Jacob had expanded the farm throughout the years, and during the 19th century sold portions of it to other farmers. That all the land came back together again as a park was due to the considerable efforts of Edward M. Bigelow, the City’s Director of Public Works.
Although the park was officially established in 1889 around the popular Reservoir No. 1, it was Bigelow’s meetings with some 120 land-owners that secured the bulk of the property. Parcel by parcel and at a cost of over $900,000, Bigelow built his park. It became a joke at City Hall that even though the City was always broke, Bigelow could somehow find money to add land to Highland Park, and this headstrong determination did not always win him friends. In 1900, he was removed from his position as Director, although he served in this capacity again from 1903 – 1906.
The piecemeal acquisition of parkland made it more difficult to create a unified plan for Highland Park than for Schenley Park, which was created in great part by one large tract of land. However, many park features that were developed in the 1890s still remain today. Christopher Lyman Magee, who is memorialized in a fountain at Schenley Plaza, provided the funds to construct a zoo, which opened in 1898 and became the city’s municipal zoo after a few specimens were transferred from Schenley Park’s small zoo. The grand Victorian entry garden was also constructed during this period, with the gateways and sculptures by Giuseppe Moretti installed in 1896. Early photographs and picture postcards reveal it to have been the finest public space in Pittsburgh and a first-rate example of the kind of municipal enrichment associated with the City Beautiful movement. Director Bigelow gave himself credit for the design of the plaza. The park’s second entrance, at the intersection of Stanton and Negley, was formalized in 1900 with the installation of two bronze Horse Tamer statues by Moretti.
Highland Park gets its name from Robert Hiland, the surveyor who was hired to subdivide the Negley lands around East Liberty. Hiland Avenue was originally the road that led into the park, but all instances of “Hiland” were changed to “Highland” by City Council in 1890.