In its day, Jennings Ordinary was a scene of lively activity. This ordinary (that is, a tavern) beside the road to Richmond served the local trade and was a stop on the stage and mail routes. Originally, a side entrance led into a three-bay hall-parlor-plan frame structure with an exterior chimney. Dining was in the basement, entertainment and dancing on the first floor, and sleeping quarters on the second floor and in the attic. In the later part of the nineteenth century, the one-bay two-story wing with an interior chimney was added, and in the 1930s the building, by then a residence, was drastically remodeled with its openings changed and window sash replaced.
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