Native Americans used this hill as a vantage point for warfare and hunting. The Apache, and later, the Comanche Indians dominated the area as they hunted along waterways including nearby Cibolo Creek. The hill was also a prominent landmark for travelers in the 18^th and 19^th centuries. The old Spanish road (one of several routes of the Camino Real or Royal Road) from San Antonio to Bastrop and Nacogdoches in East Texas extended past the base of the hill. The road followed earlier American Indian travel routes, and today its remnants are known as Nacogdoches Road.

The land surrounding and including Comanche Lookout was part of Land Grant Survey #196 comprised of 1,476 acres that was surveyed for James Conn in April 1847. The property subsequently had a number of owners including Peter W. Gray, Alexander Patrick, and Ludovic Colquhoun. Frequent sale of land grants was not uncommon during the Republic and early Statehood periods in mid-19^th century Texas.

The Comanche Lookout property was acquired by Mirabeau B. Lamar in September 1848. Lamar served as second president of the Republic of Texas (1838-41) and enjoyed a long and distinguished political, military and diplomatic career. It is not clear why Lamar purchased the land described in his deed as "including the hill known as Comanche Lookout." The property was inherited by Lamar’s daughter by his second marriage, Loretto Evalina (1852-1933) who was only seven years old when her father died in 1859. She later married Samuel Douglass Calder, also a member of a prominent Texas family. The Calders lived in Galveston and apparently did not use the Comanche Lookout property. In July 1890, they sold 524.6 acres of the land to German immigrants, Gustav and Adolph Reeh of Bexar County for $3,500. The Reeh brothers used the land for farming. After Adolph Reeh died, Gustav sold a portion of his land to retired Army Colonel Edward H. Coppock in February 1923 for $6,000.

Coppock was a romantic and history aficionado, and with assistance from his two sons and a man named Tarquino Cavazos, he constructed an extensive compound on the hill including a four-story, medieval-style stone tower. Coppock envisioned a castle-like house, but completed only its foundation. Both he and Mr. Cavasos died in 1948 and the project was abandoned. Colonel Coppock’s children sold the land in 1968 to a developer who cleared all of the structures except for the tower and some remnant foundations.

Historical photos of Comanche Lookout structures in the 1940s provided by Abel Morones, Tarquino Cavazos' grandson.

The property traded hands several times before the real estate market collapse of the 1980s led to the Resolution Trust Corporation’s ownership of the remaining Comanche Lookout property in 1990. At that time, a private sector effort was organized to preserve the site led by a group named Save Comanche Lookout. This resulted in the Trust for Public Lands providing an interim loan to the City of San Antonio to purchase Comanche Lookout for a City park. The loan was repaid through the 1994 General Obligation Bond package.

The 1994 Bond package provided $1.4 million for acquisition and development of the site. In 1995, the Parks and Recreation Department retained landscape architectural consultant, Laffoon Associates, to analyze the site and develop a conceptual plan that would preserve the park’s natural and cultural assets. The first phase of development included construction of off-street parking, level 1 and 2 accessible trails, and service roads, and installation of drinking fountains. The second phase of development will be funded with $762,300 from the 1999 Bond election. It will be completed in conjunction with construction of a branch library on the perimeter of the park at Judson and Nacogdoches Roads. Scheduled for 2003-04, Phase 2 will include additional parking improvements and trails, picnic and restroom facilities, landscaping and site work.