Windsor was located on the north bank of the Guadalupe River across from the site of present Waring twelve miles northwest of Boerne in western Kendall County. It was a stop on the stagecoach line between San Antonio and Fredericksburg. At Windsor the stage line intersected the road from Comfort to Sisterdale and Blanco. Edward Wentworth purchased land at that crossroads in 1874, built a limestone house to serve as a stage stop, and selected the name. Windsor acquired a post office in 1880, and Edward Wentworth's wife, Lucy Wentworth, became postmaster. In 1887 the San Antonio and Aransas Pass Railway built a spur line that extended from San Antonio to Kerrville with a proposed branch to Fredericksburg. The railroad line near Windsor was constructed on the south bank of the Guadalupe River and bypassed the Windsor stage stop. With the completion of the railroad, the stage route was discontinued. In 1887 the post office was moved to the new community of Waring across the Guadalupe River. In 1990 the Windsor site had several restored stone structures originally constructed in the 1870s.
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