Long before the European settlers came to Texas, the Hill Country had a network of Indian trails that had been used since pre-historic times. The modern traveler is used to following modern highways and is unconcerned by the height of the terrain and the difficulty of traversing geographic obstacles. But this was not the case for the early settlers and the native Americans that proceeded them. In those days, geographic obstacles and the height of the terrain were major considerations, and the trails tended to follow the easiest path from one location to another. Therefore, the early trails followed rivers and streams and crossed the boundaries between watersheds at the lowest possible elevations. The length of the trail was less important than the ease of traveling along it. Where high hills or areas of rough terrain were found, the trails tended to go around them. Where steep inclines were encountered, the trails did not go in a straight line but traversed the slope in a series of “switchbacks” that were more or less perpendicular to the slope.

The two most important of the trails in the central Hill Country were the Pinta Trail and the San Saba Trail, but there were innumerable less important trails that intersected or complimented the major ones.

The San Saba Trail

From the earliest explorations by the Spaniards, the San Saba Trail was used as the shortest and fastest way to travel to the Santa Cruz de San Sabá Mission near Menard, which had been established by the Spaniards for the Lipan Apache Indians in 1757. The San Saba Trail originated in the vicinity of the San Pedro Springs in San Antonio, and proceeded in a generally northwesterly direction to the vicinity of what was to later be Bandera, Texas. From there the San Saba Trail veered northeastward around an area of relatively steep and forbidding hills, and then turned north to the present site of Kerrville, where it crossed the Guadalupe River. From the Kerrville area the trail proceeded in a northwesterly direction toward the headwaters of the Guadalupe River. There, it reached a relatively open area of rolling hills. This area is where IH-10 now extends between Kerrville and Junction, and the trail generally followed the path of the present-day interstate highway.

A few miles east of Junction, the San Saba Trail reached the site of what was become Segovia. At that point it followed the Johnson Fork of the Llano River, around a high bluff that was later to become known as Cloud Point. After crossing the Llano River, the San Saba Trail crossed turned northward toward the area of the present-day city of Menard.

The Pinta Trail

The Pinta Trail also originated in the area of the San Pedro Springs in San Antonio, and proceeded in a generally northwesterly direction for approximately 180 miles to the Santa Cruz de San Sabá Mission near Menard. For the first few miles the Pinta Trail went almost due north along the path of the present day Blanco Road until it reached Salado Creek. At that point the Pinta Trail crossed the Salado Creek and proceeded up the valley of the Salado Creek toward its headwaters. Just before the headwaters of the Salado, the Pinta Trail turned rather abruptly to the west in order to pass through Puerta Pinta (the Painted Pass), which was formed by Leon Creek and provides easy access to the Hill Country north of San Antonio. The Puerta Pinta was also called the Paso de Los Apaches (the Pass of the Apaches) and the La Puerta de Las Casas Viejas (gateway to the old houses). Puerto Viejo (the Old Pass).

After passing through the Puerta Pinta, the trail moved northwest along the Leon Creek toward its headwaters, and crossed a divide, near the present-day location of Fair Oaks Ranch. Beyond the divide the Pinta Trail led downward across a broad expanse of open ground, crossed the Balcones Creek, and proceeded to the Cibolo Creek where Boerne is now located.

A few miles northwest of the Cibolo Creek crossing, the trail turned almost due north and climbed along stream beds into the hills until it crossed the boundary between the San Antonio and Guadalupe River watersheds a about five miles north of the Cibolo Creek, Seen from a distance, the divide is a solid lines of hills with a small notch that was possibly seventy feet lower than the surrounding terrain. That was the point where the Pinta Trail crossed the divide.

Once it had entered the watershed of the Guadalupe River, the Pinta Trail moved downward through the valleys formed by a succession of creeks until it crossed the Guadalupe River near the location where it is joined by West Sister Creek. That juncture and the crossing at the Guadalupe River is the approximate location of the Battle of Walker Creek, which occurred in 1844. The present Ranch Road 1376 very closely approximates the path of the Pinta Trail between Boerne and the vicinity of Highway 290, a few miles east of Fredericksburg.

Relatively little physical evidence of the Pinta Trail remains today, but its path can be inferred from the terrain, historical documents, and the orientation of streets in some towns. For example, the main street in Fredericksburg marks the path of the Pinta Trail through that area.

Beyond Fredericksburg, the Pinta Trail moved northward, generally along the path of the present-day highway US 87, to Mason. There are indications that it passed through Cherry Springs on the way, which is located several miles west of US 87. Just north of Mason, the trail turned in a northwesterly direction, passing through Koocksville and then taking a more westerly direction to Grit where it turned slightly to the northwest and generally followed the path of State Highway to the Pegleg Crossing of the San Saba River. After crossing the San Saba River, the Pinta Trail followed the river valley to the Santa Cruz de San Sabá Mission in Menard.