Fentress is at the southwestern edge of Caldwell County. A settlement, first called Riverside, began developing there in the vicinity in the late 1860. In 1892 the community was renamed Fentress in honor of James Fentress, its first doctor. The community was fortunate to be on the mail route between San Marcos and Luling. In 1918 the six-year-old Fentress water tower collapsed onto the town's only bank; cashier J. W. Lipscomb saved his life by dashing into the vault. Starting from the 1920s, nearby oilfield activity was significant in the local economy. The town served as the setting of The Evolution of Calpurnia Tate, which won the 2010 Newberry Honor Award.
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