Hickory Hill Park traces its origins to 1927 with a 40-acre (160,000 m²) parcel of wood lots and farm fields purchased for expansion of the adjacent Oakland Cemetery. Oakland expanded slowly, leaving much of the land to naturalize. An area of 50 acres (200,000 m²) was added in 1952 and the area was formally dedicated as a park in 1968, thanks to efforts of Dee Norton and other citizens.^[4] The park was expanded to 190 acres (0.77 km²) in the 1980s as part of a storm water control project.^[5] In April 2008, Friends of Hickory Hill Park raised $160,000 to purchase a 16-acre (65,000 m²) parcel that abuts the northwest edge of the park.^[6] The parcel includes wooded and open areas. The remains of an ice dam and an ice house may be found on the property.

Hickory Hill Park is irregular in shape owing to its piecemeal land acquisitions. Much of the park is steeply sloped and wooded, with large areas of abandoned fields that are slowly being naturalized. Two picnic shelter areas are available, one near the far south entrance off Bloomington Street and one in the west off Conklin Lane. A large retention dam, built in the 1990s, sits in the center of the park.^[7]

Until the 1990s, Hickory Hill Park was at the edge of the city, and the park boundaries abutted farmlands to the north and east. However, development of the First Avenue extension to the east and Scott Avenue to the north enclosed the park, and new housing and commercial developments within this area greatly reduced the potential expansion area for Hickory Hill. Expansion plans are also limited by the adjacent Oakland Cemetery, St. Joseph’s Cemetery, and Regina High School. Other threats include trail erosion, and invasive species including garlic mustard, multiflora rose, and tree of heaven.