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San Antonio's 511-acre Medina River Natural Area offers a variety of trails on the city's south side, many of which hold historical significance dating to Spanish Colonial times. The property is located on a portion of the approximately 4,400 acres of land granted to eventual Spanish Texas governor Ignacio Perez in the 1700s, and includes one of the state's oldest family ranches. In recent years, archeological investigations have revealed centuries-old activity in the area, including wheel marks in creek beds at the Dolores Applewhite Crossing that indicate its use as part of the legendary El Camino Real de los Tejas and earns the site listing in the National Register of Historic Places.

To experience the view from the Spanish Colonial period firsthand, hike the seven-mile El Chaparral Trail. From the parking lot off Jett Road, take the sidewalk westward, where subtle swales lead to the historic river crossing, also known as the Paso de Dolores. The hiking trail passes a reconstructed jacal, a structure believed to be original to the Perez Ranch, one of the earliest ranches in Texas.