The history of the Chesapeake Bay Retriever offers a very interesting story. It has been documented to show that in 1807, an English ship, that made routine trips between Newfoundland and England, became a casualty of the sea near the coast of Maryland. Not all was lost in this shipwreck and the cargo including two Newfoundland puppies and crew were rescued by an American ship that was headed for Baltimore. The surviving male dog was named "Sailor," and the female was named "Canton". The two gentlemen that took possession of these dogs were avid waterfowl hunters discovered that the two dogs were very proficient retrievers.

On breeding these two dogs with a variety of locally owned breeds they produced offspring that exhibited retrieving abilities that made them popular with the local duck hunters.

History shows that the AKC was established in 1884. By that time a pronounced Chesapeake variety of waterfowl retriever had been developed and was known for its' ability to manage the rough, icy waters of the Chesapeake Bay. Often the dogs were required to retrieve 100 or 200 ducks in a day. At that time the breed was found in one color only - dark brown, shading into a sort of reddish brown. Their head was wedge-shaped and their coats were thick and long. Several lines of Chesapeake Bay dogs were produced as early as 1880, under a variety of breed names that included the Chesapeake Bay Duck Dog, the Brown Winchester, the Otter Dog, the Newfoundland Duck Dog and the Red Chester Ducking Dog.

In 1890 the name was finally given as the Chesapeake Bay Retriever. This is when breeding records were started and Baltimore's Chesapeake Bay Dog Club was formed. Today the breed is active in all areas of AKC competition. In 1964 the Chesapeake Bay Retriever became the official dog of the State of Maryland.

The American Chesapeake Club holds Working Dog Tests called "trials". When a dog passes all the tests of a particular level, he gets a Working Dog Certificate (WD). The Working Dog test consists of simple single retrieves on land and water with appropriate birds. The dogs only have to bring the bird to within two feet of the handler to pass.

There is a more advanced test called Working Dog Excellent (WDX). In order for a dog to earn this title he must be steady to shot and do double land and double water retrieves and deliver to hand. In the middle of the 1980s, The ACC introduced a new working certificate title. This new level was called the Working Dog Qualified (WDQ). This most advanced test requires a dog to be steady, do multiple retrieves over land and water and run blind retrieves and stop on a whistle and take hand signals to a downed bird. These titles are all recorded with the American Chesapeake Club but do not show on an AKC pedigree. These titles are often referred to when determining the potential quality of new puppies.