The very first settlers in this county were Thomas W. and Anne Parker and their family, Quakers from Randolph County, North Carolina in 1814, from which the county was named. Once the county was established in 1818, five early settlers donated land for a county seat in Winchester, it’s largest city. It has remained the seat for nearly two centuries. The history of the county is distinguished by its embrace of abolitionism. One of the world’s oldest and fastest high bank half-mile race tracks, Winchester Speedway, is located north of Winchester. Also, Mrs. Wicks Pie Factory is in Winchester. It was a great place enjoy pie!