Beginning in 1845, German immigrants of the Adelsverein colonization company became the first settlers to venture significantly north of San Antonio de Bexar. From their first staging ground at New Braunfels, they began plans for a second at Fredericksburg, a way station on the journey to their promised lands north of the Llano River.

The best-known pathway into the frontier to the north was the Pinta Trail, said to be an ancient native trace. The trail began at San Antonio, crossed the Guadalupe River near today’s Sisterdale, and ventured north at least as far as the vicinity of Fredericksburg. It remained the principal gateway to the northern German settlements until the early 1850s, when its lower reaches fell into disuse in favor of a new road, known as the road from San Antonio to Fredericksburg, or some variant of that modest and obvious label. Today, its remnants are known as the Old Fredericksburg Road.

A cutoff at Boerne from the newly popular Fredericksburg Road preserved access to Sisterdale and beyond to Fredericksburg via the Pinta Trail. The trail continued to be used above Sisterdale for a period of time, but a new road from Sisterdale through Luckenbach to Fredericksburg emerged and that development, along with the rise of the Fredericksburg Road, doomed the upper Pinta Trail by the 1880s.