Although Chester is a short drive west of Peggy’s Cove, you’ll be forgiven for thinking you’ve taken a wrong turn and ended up in Maine or Massachusetts. New England planters settled the site in 1759, and their numbers were later bolstered by Loyalists escaping the American Revolution and Boston Brahmins who simply wanted to escape the city in summer. Thanks to the clapboard saltboxes and Cape Cod–style homes they left behind, Chester still calls to mind a classic New England community. Most visitors are content to explore its tree-shaded lanes or make forays into the surrounding countryside. Yachtsmen invariably stick close to the water.


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