The area around Jacob's Well was roamed by the Tonkawa, the Jumano, and later the Comanche before early settlers pushed out the Comanche, and because these groups were semi-nomadic, little evidence of them remains today. Jacob's Well Natural Area consists of five land surveys tied together by using the spring as a corner, surveys conducted by Bartlett Sims in 1847. The three surveys on one side of the spring were donated to the heirs of men who fought and died in the Goliad Massacre in 1836. In the early 1850s, William C. Winters, a San Jacinto veteran and early settler of Wimberley, followed Cypress Creek in search of its source and found an overflowing spring, which he reportedly likened to a well in Bible times, giving Jacob's Well its name. Since then, local people have been drawn to its cool, clear water, and it remains a popular recreational destination that attracts visitors from around the world. Before automobiles became widely popular, travelers in the 1800s and early 1900s reached places like Jacob's Well by horse-drawn vehicles over rough dirt roads, as shown by Southwest Texas Normal School students traveling there for a senior picnic in 1913 with Mount Baldy, once called Mount Alberta, visible in the distance as one of the Twin Sisters Mountains. After the drought of the 1950s, heavy rain washed gravel from the dry creek bed into Jacob's Well, and local landowners financed a dragline to clean out the well and then built a concrete weir around it to keep it from filling in again; that weir still stands today.