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In 1883 George Ellwanger and Patrick Barry gave the City of Rochester 20 acres of their nursery for use as a park. The Rochester Parks Commission hired the landscape architecture firm F.L. & J.C. Olmsted, to design the park as an arboretum. Olmsted created a Picturesque park that incorporated the adjacent city reservoir and afforded scenic views of the city. His plan saw Pinnacle Hill planted with pine trees to the north and arrangements of shrubs to the south. An adjacent meadow was framed by shrubs and trees. A winding drive ascended the hilltop to the park’s focal point, a three-story Children’s Pavilion designed by Shepley, Rutan, and Coolidge. Park superintendent Calvin Laney and horticulturist John Dunbar helped realize the park’s design. Over time, Dunbar changed the park’s planting palette to emphasize ornamental flora. The Lamberton Conservatory was added to the park in 1911, in addition to two land parcels, including the estate of Horatio Gates Warner in 1951. The Children’s Pavilion was destroyed in 1963, and the Lamberton Conservatory was reconstructed in 2007. 

Early-twentieth-century residential subdivisions and the Mount Hope Cemetery frame the 150-acre park. Both Reservoir Avenue and Highland Drive divide the park north to south. A curvilinear walkway follows Olmsted’s original circulation system to encircle the reservoir before summiting the hilltop and descending the park’s southeastern slope. The path winds down the hillside through plantings of magnolia, lilacs, and pansies, crossing Highland Avenue to reach a series of memorials, including the Greater Rochester Vietnam Memorial and The AIDS Remembrance Garden. East of Pinnacle Hill is a wooded park area that includes a lily pond, a natural amphitheater and bandshell known as the John Dunbar Memorial Pavilion, and Warner Castle, with its sunken gardens designed by landscape architect Alling DeForest in 1930.  Highland Park is a contributing feature of the Municipal Park System of Rochester, listed in the National Register of Historic Places in 2003.