The Sisterdale settlement, the second oldest in the Texas HIll Country, established in 1847, attracted a group of German "free thinkers".  Believing they would be able to farm part of the day and spend part of the day studying poetry, literature and music, they quickly realized they knew nothing about farming and survival would consume most of their time.  After the initial settlement, Sisterdale enjoyed continued growth over the next few years with the influx of Germans fleeing the failed European revolution of 1848.

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The 1885 cotton gin, which houses the Sister Creek winery, was in operation until 1927.  At that time, the boll-weevil infested the cotton fields in the Sisterdale valley.  Inability to eradicate this infestation eventually forced the closing of the cotton gin.