Located just below the headwaters of the San Antonio River, Brackenridge Park and the surrounding area has been a gathering place since prehistoric times. There is evidence of human visitation and occupation extending back at least 11,000 years. Native American artifacts dating as early as 9200 B.C. have been found in the Olmos Basin and near Hildebrand Avenue.

Following the founding of San Antonio in 1718, early Spanish settlers used the San Antonio River as a source of water for hand-dug ditches that irrigated their fields. Two of these ditches acequias- branched from the river in today's park. The Alamo Madre ditch was built in the 1720s and ran east, carrying water to Mission San Antonio de Valero (the Alamo). This ditch left the river opposite the back to the Witte Museum. The Upper Labor ditch was built about 1776 and watered land west to San Pedro Creek. The dam that diverted water into the ditch was excavated in 1996 just below Hildebrand Avenue. Remnants of the Upper Labor acequia remain visible within the boundaries of the San Antonio Zoo.

This area of San Antonio remained largely undeveloped until the mid-19th century. An unsuccessful attempt was made in 1839 to found the town of Avoca in the area of today's Alamo Heights. It was not until 1852, when the City began disposing of its public lands, that construction began this far north of downtown. That year, the City sold the Headwaters of the San Antonio River to a City alderman, J.R. Sweet who built his home there. A short distance to the south, the City began leasing its hard rock quarry for commercial use. During the Civil War, the Confederacy used land in today's Koehler Park for a tannery to produce leather for military supplies.