The roots of Lost Draw spread deep within the Hill Country and as far as the High Plains of Texas. In the early 2000s, High Plains-based farmer Andy Timmons diversified his agricultural operations to include grape growing at the original Lost Draw Vineyard's site. His nephew, Andrew Sides, worked for the family farming operation and helped to expand the vineyards from 5 acres to over 50. Andrew would go on to Texas Tech to study engineering, but his passion for grape growing never faded, and several years after graduating, he made the decision to pursue a career as a winemaker. At the time, Andrew's father-in-law Troy Ottmers had available historic land in downtown Fredericksburg. Andrew and his uncle Andy had Texas grapes to make and sell wine with. Everything came together and Lost Draw produced its first vintage in 2012 and opened its tasting room doors for the first time in 2014.