Chester was officially founded in 1759 as the Shoreham grant, although French fishermen had already built a few houses on the site. The first permanent European-descended settlers were a group from Massachusetts who came to the area in 1761. The village is home to the Chester Playhouse one of the best-known community theatres on Nova Scotia's South Shore. Scenes for several films, miniseries, movies of the week, and television shows have been shot in and around Chester.