Woolwine is an unincorporated community in northern Patrick County, Virginia, United States. The western terminus of State Route 40 is here, at State Route 8. The community lies in the Rocky Knob American Viticultural Area. Three covered bridges are located in Woolwine: the Jack's Creek Covered Bridge (built 1914), the Bob White Covered Bridge (built 1921) and the more recent Clifford Wood Covered Bridge (built 1977) which is privately owned. All three covered bridges span the Smith River.