Pleasant Hill Winery may be the oldest winery in Washington County, but its history began long before the first grapes were crushed on its grounds. Founders Bob and Jeanne Cottle shared a lifelong passion for winemaking; both came from Italian families and inherited winemaking equipment from their grandfathers, which the Cottles used to produce home vino in their basement for years. But when their love for winemaking outgrew the space available to them, Bob and Jeanne knew it was time to take their skills pro.

Two decades later, Pleasant Hill Winery has racked up a sprawling list of awards for its wines, which utilize grapes grown right here in Texas. But even more than medals and ribbons, the Cottles like to show off their magnificent grounds, inviting guests to tour and taste on weekends year-round.