Winchelsea, founded in 1288 by Edward I, is located in East Sussex ("1066 Country") about a mile inland from the current coastline. The town was laid out in a grid pattern of streets, as is clearly still visible to the present day (see maps for more details). It lies approximately two miles from Rye and seven miles from Hastings. Almost the entire town is a designated Conservation Area and most of the surrounding land is owned and managed by the National Trust. Many buildings in the town are Grade I or Grade II listed. The present town replaced an earlier town of the same name, sometimes known as Old Winchelsea, destroyed by storms in the late 13th century.

Winchelsea claims to be the smallest town in Britain to have its own Mayor. The Mayor and Corporation lost their civil and judicial powers in 1886 but were preserved by an Act of Parliament in order to maintain the town's membership of the Confederation of Cinque Ports. They retain both a ceremonial role and responsibility for a number of the ancient monuments of the town, including the historic Court Hall, the medieval town gates (Strand Gate, New Gate and Pipewell Gate), the Town Well and a number of other important sites.