Bill and his family moved several times in his youth, including to Sioux Falls, SD., Sheboygan WI., Milwaukee, WI., and then to Waycross, GA., where in 1937 his father purchased the General Lee Motor Court and Restaurant. Bill graduated from Waycross High School in 1942. Immediately thereafter he joined the U.S. Army Air Corps, serving for more than three and one half years. In the service he attended Auburn University and Cannisius College, became a pilot for B-25 airplanes, and served as a flight instructor and patrol duty pilot along the Mexican border near Del Rio, Texas.
The Winkenwerder family moved to Asheville in 1942 when Bill’s father took ownership of the Tour-O-Tel Court and Restaurant on Merrimon Avenue. In subsequent years the family built and owned the Town-O-Tel Court, the Mountaineer Court, and Wink’s Drive-In, a popular place for young people, with its’ own radio tower, in the late 1950’s and early 1960’s.
In 1963, Bill and his brother Jim opened Horne’s Motor Lodge on Tunnel Road, which later became the Ramada Inn of Asheville. For many years it served as one the area’s most popular destinations, hosting celebrities such as Mickey Mantle, Roger Maris, Johnny Unitas, Roman Gabriel, Richard Petty, Michael Jordan, Joe Frazier, Jerry Lee Lewis, Conway Twitty, Chubby Checker, and Milton Berle. During the inaugural season of the Atlanta Falcons Football Team, the entire team stayed at the hotel during a summer football camp.