Pilots' Rest occupies a former shop on Sheerness High Street previously home to a micropub called the Flying Sheep. It was opened in August 2023 by Neil Webb, known locally as Rock, a Rochester resident who works as a visitor experience assistant at the Wellcome Collection museum in London and continues that job part-time while running the pub. The interior is fitted out with an aviation theme, a reference to Sheppey's history as a birthplace of early British aircraft manufacture and flight. The pub is independently run rather than tied to a brewery or pub company, and serves cask beers alongside a selection of European bottled beers and meads. It opens Tuesday to Friday from 4pm to 10pm, with a later start of 6pm on Wednesdays, and Saturday from 2pm to 10pm, closing on Sundays and Mondays.
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