"... About 1712 the Roy and Buckner families became closer as John married Dorothy Buckner Smith – daughter of Richard Buckner. (Richard was John Buckner’s son.) She was also the widow of Charles Smith (of the Lawrence Smith family) and she had blood ties to the Fitzhugh’s of King George Co. John and Dorothy had a fairly large and interesting family. Among their children were ...
... John Roy’s wife, Dorothy, deserves special mention in the Roy family annals and in the founding of Port Royal. She is regarded as one of America’s first business women. In a day when men controlled everything and women had few rights, Dorothy was ahead of her time. It was she who is credited with getting a “rolling road” built connecting Chesterfield (west of Bowling Green) to Roy’s warehouse – generally following the current US 301 route. (This was to counter the road between the plantations at Guinea & Francis Conway’s warehouse.) Following the death of her husband in 1734, Dorothy obtained a license and operated a tavern in town, and secured title to both the Roy warehouse and a ferry in her name. She may have been the first woman in Virginia to own a tobacco warehouse. She died in 1746."
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[Note: No sources given.]