Winedale was located in far northeastern Fayette County four miles northeast of Round Top. The original community began around 1870 as a German settlement named Truebsal, which grew up just across the line in Washington County near the store of Charles Windewehen. The community eventually included a church and a nearby gin. In 1879, sometime after local farmers began cultivating grapes, a post office was granted with the name Winedale. It closed in 1881, and it is not clear precisely when the town moved some two miles down the road to its location in Fayette County. The new site centered around an inn known as Sam Lewis's Stopping Place on the Sawyer and Risher stage line from Brenham to Austin. Samuel K. Lewis purchased the original 145-acre William Townsend homestead from Capt. John York in 1848, added an adjoining tract of 640 farm acres, and expanded the one-room house to make it suitable for an inn, more than doubling its size and converting the loft into a second story. By the twentieth century the town had ceased to exist. The Lewis home and farm, however, became the centerpiece for the development of the Winedale Historical Center beginning in the 1960s. The population was forty-one in 2000.
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