Old Bowling is a rural community located at the end of Farm Road 1147 about fourteen miles west southwest of Centerville in western Leon County. Settlement in the region had begun by the late 1850s and early 1860s, and the community was named for one of the first settlers, a minister named Boling. Farmers spelled the name as Bowling. One of the earliest structures was a two-story building that eventually functioned as a school, church, community center, and Masonic lodge. Pioneering families included the Vestals, Allisons, Bolings, Caldwells, and Wilsons. In 1868 the Allisons and Vestals operated a steam gin. The first school opened around 1870, and the Masonic lodge was organized in 1871 and operated until 1875. Bowling had a post office from 1858 to 1866 and from 1871 to 1873. By the late 1870s the community also had a general store, saloon, and blacksmith. The school continued to serve area farming families until it closed in 1929, when Bowling consolidated with the nearby Concord school. In the 1950s the community held annual homecomings each May. In 1965 the Old Bowling School and Masonic Lodge received a Texas Historical Marker. Population estimates for the settlement, now called Old Bowling, reported twenty residents in 1990. That figure remained constant in 2000. The historic school building and a cemetery are the visible remnants of the old community.
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