Chesapeake Bay Retrievers trace their history to two pups who were rescued from a foundering ship in Maryland in 1807. The male 'Sailor' and female 'Canton' were described as Newfoundland dogs, but were more accurately Lesser Newfoundland or St. John's Water Dog. These two lived in different parts of the bay area and there is no record of a litter being produced together. They were bred with area dogs, with more consideration given to ability than to breed, to create the beginnings of the Chesapeake Bay Retriever breed.

There are few records of the breeds of these early dogs, but spaniels and hounds were included. Dogs from both Chesapeake Bay shores were recognized as one of three types of Chesapeake Bay Ducking Dog in 1877. In 1918 a single type, called the Chesapeake Bay Retriever, was recognized by the American Kennel Club, and there have been few changes to the breed standard since then.

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