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The gap in the mountains north of Huntly was named after Captain Thomas Chester who bought a tract of land on the west side in the 1700's. It is referred to by that name in the journals of soldiers who had to march over the mountain during the Civil War, and includes a settlement formerly called Williamsburg because of the number of Williams families that lived there.
Bradley Williams, who has been running the gen( eral store on the mountain since 1977, said that in his childhood the families who lived in Chester Gap found employment at one of the two large orchards, one called Chester Gap Orchard, run by the Woods, and one run by the Norths.
Chester Gap orchard, said Williams, was so large that it included its own store and its own barrel-making operation. Williams said that most families on the mountain grew corn and pastured their cows and hogs up in the mountain woods.
“The cows had bells,” said Williams, “so that if one was missing at milking time, it wasn’t such a hard matter to find it.”
Transportation in those days consisted of horses and wagons and Chester Gap residents also were used to the long steep walk from their homes to Front Royal. “We didn’t mind it,” remembers Williams, “but of course we didh’t know any different. In fact, most folks anywhere didn’t know any different, so it never seemed that life here was harder than anywhere else."
At the bottom of the settlement in the 1940’s was the Appalachian Inn, a dance hall establishment run by Owen Sealock. “It got a bit rowdy there at times,” said Williams, who remembers folks from Front Royal, Flint Hill, and as far away as Sperryville coming to dance at Chester Gap.
The weather up on the mountain has always been uncertain. Fog hangs over the mountaintop even on days that are clear elsew'here, and the high altitude explains the heavy snowfall. “We used to be able to walk on the snow over the fences,” Williams recalls.
The hard-working farm families found employment at the orchards from September to December.Everyone had a patch of corn, which Williams allows
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