The Pinta Trail was used by natives, explorers, and settlers to travel between today's San Antonio and the vicinity of today's Fredericksburg. It was probably part of the trail network used by Jumanos in the seventeenth century to journey and trade among New Mexico, Central Texas, La Junta de los Ríos, and East Texas. After Spaniards established the San Antonio de Bexár Presidio in 1718 and the villa of San Fernando de Bexár in 1731, the Pinta Trail was one route used to explore to the north. It was also a north-south route for Apaches, who migrated southward into the Texas Hill Country not long before Spaniards crossed the Rio Grande and began exploring Texas. The trail was one route to the short-lived Spanish mission and presidio at San Sabá, and was part of the return path taken on a 1767 frontier inspection by the Marqués de Rubí.
Once the Spaniards abandoned San Sabá in 1768, only hardy and well-armed explorers ventured far north of San Antonio; it was a period that saw the Comanches push the Apaches farther south and claim the Texas Hill Country as their own. For the most part, the Pinta Trail reverted to a native pathway.
After German immigrants established New Braunfels in 1845, they forged onward to found Fredericksburg using a trail that looped south from New Braunfels and connected with the Pinta Trail above San Antonio, converting the trail to a road for European settlers. But the trail between San Antonio and Sisterdale was rugged, particularly in its upper reaches. A more forgiving trail from San Antonio, known as the Camino Viejo, ran near the future site of Boerne, about eight miles west of the Pinta Trail. Soon after Boerne was established in 1852, settlers built a new wagon road from there to Sisterdale, and the road quickly became the favored route from San Antonio to Fredericksburg. Use of the lower Pinta Trail declined; by 1854 it was virtually abandoned.
From San Antonio, the Pinta Trail ran to the east of Olmos Creek northward to near the Balcones Escarpment, and then angled to the northeast through the escarpment to intercept Salado Creek, using the passage that is today's Northwest Military Highway. Instead of using that route, some travelers may have used the narrow Salado Creek Canyon to traverse the escarpment. Once in the valley that is today's Camp Bullis, the trail followed Salado Creek, passed Comanche Spring near the southeast corner of Camp Stanley, and then forded Cibolo Creek downstream of Balcones Creek, near the mouth of Post Oak Creek.
Post Oak Creek carves a passage through a high amphitheater of hills above Cibolo Creek; Spaniards knew that daunting ridge as los Balcones, and, though Cibolo Creek was an early and well-known landmark, they sometimes referred to Cibolo Creek as the Arroyo de los Balcones. After crossing Cibolo Creek, they followed Post Oak Creek to ascend the promontory—it was there that the rugged stretch of the Pinta Trail began, as it trended north-northwest, crossing Spring Creek, Sabinas Creek, and Wasp Creek.
Above Wasp Creek, most travelers crossed the Guadalupe at the reliable crossing that is Farm Road 1376 today. In December 1839 Bexar County deputy surveyor and Texas Ranger John C. "Jack" Hays surveyed the tract above that ford and noted the presence of the "Paint Road," which became the route for ranger patrols into the wilderness; not much farther along the Pinta Trail was the site of Hays's famous 1844 battle at Walker's Creek.
In January 1847 Ferdinand von Roemer rode the Pinta Trail and used a Guadalupe River crossing farther downstream, at Cypress Bend; he was traveling with John Meusebach to the six-month-old village of Fredericksburg and onward to San Sabá. This ford does not appear on survey maps of the period, and it serves to demonstrate that early trails branched and shifted and that river fords were not exact points.
In September 1847 Nicolaus Zink bought a tract north of the upstream crossing and was joined by Ottomar von Behr, who purchased a tract on the south side of the crossing in February 1848, seeding the community of German Freethinkers that became Sisterdale and establishing the upstream crossing as the preferred ford.
Above today's Sisterdale, the trail followed West Sister Creek to the vicinity of its headwaters, then diverted to the northwest along Jung Creek, traversed a ridge and dropped down to ford South Grape Creek. Continuing northwest, it crossed the Pedernales at the first inverted horseshoe bend east of Baron's Creek, north of today's U.S. Highway 290, where United States Boundary Commissioner John Russell Bartlett visited the Mormon colony of Zodiac in 1853, shortly before it was devastated by a flood. Because the trail above West Sister Creek was another difficult stretch of the trail, it was soon abandoned in favor of a road up a gentler slope to the east, passing through Luckenbach.
It appears that the trail originally passed Fredericksburg to the east, but the town's founders built roads through their settlement. The name "Pinta Trail" was not used beyond that point, even though ancient trails continued to the northwest. Today, much of the Pinta Trail has been abandoned and is no longer visible.