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The pub stands on the site of a Hermitage which was a stopping point for pilgrims on their way to Canterbury. At the time of the dissolution of the monasteries it was given to a Thomas Jennings. Ogilby's map of 1675 shows that an inn was present on this site at this time. The current building is C19. See http://www.britishlistedbuildings.co.uk/en-112655-st-anne-s-castle-inn-great-and-little-le for details.