The Pinta Trail
The Pinta Trail began as a natural footpath for Native Americans traveling through the Hill Country. First used in the 17th century, it is one of the oldest paths followed by humans in this part of the world.
In the 1750s, Spanish priests and soldiers traveled the Pinta Trail from their base in San Antonio to the San Saba mission and presidio near present-day Menard.
When the German Texans came up from Indianola, they followed sections of the Pinta Trail into the relatively uncharted Hill Country.
Surveyors, rangers, teamsters and adventurers used the Pinta Trail. Jim Bowie followed it in search of the lost San Saba mine.
After the U.S. Army built Fort Martin Scott and later Fort Mason, the Pinta Trail became an army supply route from San Antonio to the western outposts.
And when surveyors laid out a stagecoach road from San Antonio to El Paso, the path generally followed the Pinta Trail through the Hill Country.
The trail’s original location was no accident. When the Plains Indians traveled, they usually followed the buffalo. They knew the buffalo instinctively followed the easiest grades with the lowest mountain passes and the best low-water crossings.
The origin of the name “Pinta” is steeped in legend, and, like so many place names in Texas, it has been garbled by centuries of misspellings and mispronunciations in several languages. Pinta may be a derivative of “pinto,” the distinctive color patterns of the Indian pinto ponies.
The Pinta Trail was not always a single narrow path but was often comprised of several branches that ran in the same general direction. The width of the trail ranged from a few feet to several miles.
And the location was not constant. Sometimes events of nature like floods and landslides caused the trail to shift.
Although the exact route is often vague, the Pinta Trail ran from the missions on the San Antonio River, to Leon Springs, to just east of Boerne. From there the path ran northwest, passing near Sisterdale and then crossing South Grape Creek near Grapetown. After that the trail swung through the pass at Cain City, crossing the Pedernales River at the bend just east of the mouth of Barons Creek, a mile south of Fort Martin Scott.
B.L. Enderle, Gillespie County teacher and surveyor, was a student of the Pinta Trail, and he believed the ancient road took two paths out of Fredericksburg.
One path went to Cherry Spring and Loyal Valley, crossing the Llano River near Hedwig’s Hill, and on to Mason. The other branch went in the direction of Bear Mountain and into Crabapple Canyon before crossing Sandy Creek near Enchanted Rock. The trail then curved back to the northwest towards Mason.
Travel along the Pinta Trail could be hazardous. In June 1844, Captain Jack Hays and a group of 14 Texas Rangers that included Ad Gillespie, Ben McCulloch and Sam Walker fought a pitched battle with Chief Yellow Wolf and 80 Comanche warriors near the Guadalupe Crossing on the Pinta Trail.
The Rangers were heavily outnumbered, but they had a huge technological advantage. It was the first time an entire company of Rangers used Colt revolvers in combat.
The battle raged for hours, but after Gillespie dropped Yellow Wolf with a rifle shot, the remaining Comanches retreated to the northwest.
Although most visible signs of the Pinta Trail have vanished, many modern roads and highways follow parts of the old route. Northwest Military Highway out of San Antonio, Interstate 10 between San Antonio and Boerne, U.S. Highway 87 between Fredericksburg and Mason, Ranch Road 965 from Fredericksburg to Enchanted Rock, and Texas Highway 29 from Mason to Menard, generally follow segments of the old Pinta Trail.
And it was no coincidence that the railroad from San Antonio to Fredericksburg followed stretches of the Pinta Trail. After all, the buffalo and the Indians had already plotted the course, and they did it without a transit or an engineering degree.