Watterson, located in southern Bastrop County about nine miles south of Bastrop on an old road between Bastrop and Red Rock, is named for pioneer Charles Coffin Watterson, who with his wife, Martha, settled in the area about 1852 and began farming and stock raising. Samuel and Caroline Wolfenbarger were also among the community's early settlers, most of whom depended on farming and stock raising for a living. A post office with the name Live Oaks was established in 1878 with Watterson as postmaster. In 1891 the town was renamed in his honor. In 1896 the community had a population of 100, a Methodist church, a gristmill and gin, and a general store. Students attended the Lentz Branch and Hilbig schools, which combined as the Watterson school in 1900. The post office closed in 1904, and the Watterson school was consolidated with the Eight Live Oaks school in 1927. A school for black children was also located in the area at this time. In the 1930s Watterson still had a community club and Methodist church. By 1962 many of the large farms had been broken up, but Watterson remained a farming community made up in large part of descendants of the early settlers. Though no population figures appear for it in any twentieth-century Texas Almanac, in the mid-1980s Watterson continued to be listed as a community in Cities and Towns of Texas and to appear on county highway maps.
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