Crockett Square, bisected by Main Avenue and frequently called the "Twin Parks," was established as a public space in 1875. That year, the City of San Antonio settled a lawsuit over ownership of a tract that extended south to the Upper Labor irrigation ditch near today’s Euclid Street, and west to the San Pedro ditch near San Pedro Springs Park. As part of the settlement, the City agreed to "keep forever that certain oblong square of ground…….as one of its public squares."

It was several years before homes were built as far north as the square and new residents began to clamor for the park’s improvement. Soon after the City’s first streetcar line began its run to San Pedro Springs in 1877, real estate developers offered land for sale and building sites quickly replaced pastures and gardens. By August 1883, citizens petitioned City Council to enclose Crockett Square, clear brush from the park, and lay out and mark the streets running through the square. The Council agreed to clean the park using City prisoners, but refused to enclose the area. (Parks were enclosed at that time to keep livestock from damaging plants.)

Council minutes reveal the condition of the landscape and City infrastructure in the early 1880s. "…as there being no water convenient, it would be almost impossible for any tree or plant to live in that locality." Crockett Square remained a bleak spot at least until 1886 when the Council finally agreed to spend $215 to enclose the park "with a fence similar to that around Milam Park." Though no description of the fence has been located, other public spaces of the period were enclosed with whitewashed, wooden plank fencing.

There are few known accounts of the park’s appearance in subsequent years. In 1896, City Council directed that holes and gullies at the east end of the park be filled with dirt excavated from new sewer trenches on Main Avenue. According to City Engineer’s drawings in 1911, a new 5-foot wide sidewalk was constructed around the park’s perimeter, and in 1914, walks were built within the two squares. The completed plan was formal in design, with internal walks radiating from a central, circular sidewalk to the corners of the square.

This pattern remained until 1957 when Crockett Square was remodeled as "a study in modern park planning." The new plan created one large turf area watered by a sprinkler system. Beginning in the early 1980s, the Tobin Hill Neighborhood Association began raising funds to improve Crockett Square. Interested individuals then formed the Crockett Club and worked with institutions and groups including Metropolitan Hospital and the Downtown Optimist Club to install picnic tables, plant trees, and construct a playscape. In the late 1990s, park rehabilitation also included new sidewalks, lighting and drinking fountains. These improvements were funded through $233,000 in 1994 Park Bond and Community Development Block Grant funds.