The Pinta Trail (Camino Pinta) was a natural pathway through the Hill Country, utilized by Native Americans and later linking to Spanish settlements to the southeast. The path extended about 180 miles northwest from San Antonio to the 1750s Spanish presidio at Menard. In the 1780s, pathfinder José Mares incorporated the link into a shorter route between Santa Fe and San Antonio. Maps, surveys and contemporary accounts include many variations of Pinta, all said to derive from the Spanish word pintar (to paint). Pinto ponies or the Piedra Pinta Mountains on period maps are two possible explanations. In 1839, John (Jack) Coffee Hays surveyed the area where the Pinta Trail crosses the Guadalupe River, designating the route as Paint Road. It became a consistent map feature soon after Texas statehood. In the 1840s, the German Adelsverein utilized the trail for access to its new settlements near the Pedernales River. Naturalists Ferdinand Lindheimer and Ferdinand von Roemer referenced the Pinta Trail in their 1845-47 excursions. Nicolaus Zink settled along the path in 1847, becoming the first pioneer in the future colony of Sisterdale. The trail's use diminished when new routes were established. Landscape artist Hermann Lungkwitz documented the historic road in his painting Old Pinta Crossing on the Guadalupe (1857). The trail went through the center of Kendall County. East of Boerne, it crossed the southern boundary of George Wilkins Kendall's ranch west of Post Oak Creek. The selection of the Pinta Trail as an ancient pathway stood the test of time. By connecting reliable water sources, good terrain and emerging settlements, the trail was an important factor in the development of the Hill Country and Kendall County. (2013)