Fentress is on the San Marcos River at the southwestern edge of Caldwell County. A settlement, first called Riverside, began developing there in the vicinity of a Cumberland Presbyterian church established in 1869. A horse-powered cotton gin was built in the vicinity about 1870 by the partnership of Cullen R. Smith and Joseph D. Smith. The enterprise was moved to the riverfront and converted to waterpower in 1879; it was operated by family members until it closed in 1968. In 1892 the community was renamed Fentress in honor of James Fentress, its first doctor; he was also a large landholder and a participant in the battle of Plum Creek. A year later a post office was established in W. A. Wilson's general store, with Wilson as postmaster. The community was then on the daily mail route between Luling and San Marcos. A one-room school, which operated for three months each year, opened in 1895. An 1896 business directory lists a doctor, a blacksmith, and a population of 150 in Fentress. The Fentress Waterworks was established in 1898 and a lighting system in 1902. The Fentress Telephone Company was formed soon after 1900, and around 1904 the community had its own newspaper, the Fentress Indicator. In 1905 a Methodist congregation was organized, and four years later they built their own church. In 1907 the one-room school was replaced with a two-room structure that served until 1922, when a two-story, five-room facility with an auditorium was completed. A 1915 business directory lists Fentress with 300 residents, three general stores, a mercantile company, a meat market, a confectionery, a pharmacy. a gin, and a blacksmith shop.
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