
The town was sacked twice during the 100 years war with France and, after the second attack, the estuary was closed by a chain every night and the narrow mouth was protected by two fortified castles, Dartmouth Castle and Kingswear Castle. Dartmouth also had the dubious distinction in medieval times of being a major base for "privateering", AKA state sanctioned and licensed piracy.

Dartmouth sent numerous ships to join the English fleet that attacked the Spanish Armada in the 17th century and the Spanish Armada's "payship", commanded by Admiral Pedro de Valdés, was captured along with all its crew by Sir Francis Drake. Local folk lore tells how the ship was reportedly anchored in the river Dart for more than a year while the crew were used as laborers on the nearby Greenway Estate. Centuries later, Greenway was to become the home of Dame Agatha Christie.
In the latter part of World War II the town was a base for American forces and one of the departure points for Utah Beach in the D Day landings. Much of the surrounding countryside was closed to the public while it was used by US troops for training.
More pictures of this backwater treasure are here.
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